Product Name

  • Name

    Methyl (E)-2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxyacrylate

  • EINECS
  • CAS No. 131860-97-4
  • Article Data30
  • CAS DataBase
  • Density 1.305 g/cm3
  • Solubility
  • Melting Point
  • Formula C15H13ClN2O4
  • Boiling Point 469.279 °C at 760 mmHg
  • Molecular Weight 320.732
  • Flash Point 237.612 °C
  • Transport Information
  • Appearance
  • Safety
  • Risk Codes
  • Molecular Structure Molecular Structure of 131860-97-4 (Methyl (E)-2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxyacrylate)
  • Hazard Symbols
  • Synonyms Benzeneaceticacid, 2-[(6-chloro-4-pyrimidinyl)oxy]-a-(methoxymethylene)-, methyl ester, (E)-;Methyl(E)-2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxyacrylate;Methyl(E)-2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxypropenoate;
  • PSA 70.54000
  • LogP 3.08260

Synthetic route

4,6-dichloropyrimidine
1193-21-1

4,6-dichloropyrimidine

C12H15O5(1-)*Na(1+)

C12H15O5(1-)*Na(1+)

(E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate
131860-97-4

(E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate

Conditions
ConditionsYield
Stage #1: 4,6-dichloropyrimidine; C12H15O5(1-)*Na(1+) With sodium carbonate; methyl 1,4-diazabicyclo<2.2.2>octane-2-carboxylate In toluene at 20℃; for 2h;
Stage #2: With zinc(II) chloride In toluene for 6h; Solvent; Reagent/catalyst; Reflux;		97.3%
methyl (Z)-2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxyacrylate

methyl (Z)-2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxyacrylate

(E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate
131860-97-4

(E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate

Conditions
ConditionsYield
With methanesulfonic acid In acetonitrile at 70℃; for 8h;96.9%
3-((α)‐2‐(2‐(6‐chloropyrimidin-4‐yl)oxy)phenyl)methyl-3-methoxyacrylate
383428-73-7

3-((α)‐2‐(2‐(6‐chloropyrimidin-4‐yl)oxy)phenyl)methyl-3-methoxyacrylate

(E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate
131860-97-4

(E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate

Conditions
ConditionsYield
With methanesulfonic acid for 1h; Heating; Large scale;96%
With methanesulfonic acid In toluene at 85℃; for 1.5h; Large scale;
methyl 2-(2-((6-chloropyrimidin-4-yl)oxy)phenyl)acetate
484064-87-1

methyl 2-(2-((6-chloropyrimidin-4-yl)oxy)phenyl)acetate

dimethyl sulfate
77-78-1

dimethyl sulfate

trimethyl orthoformate
149-73-5

trimethyl orthoformate

(E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate
131860-97-4

(E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate

Conditions
ConditionsYield
Stage #1: methyl 2-(2-((6-chloropyrimidin-4-yl)oxy)phenyl)acetate; trimethyl orthoformate With titanium tetrachloride; triethylamine In dichloromethane at -5 - 20℃; Inert atmosphere;
Stage #2: dimethyl sulfate With N-benzyl-N,N,N-triethylammonium chloride; sodium hydroxide In water; toluene at 20 - 50℃;		91%
...Expand
4,6-dichloropyrimidine
1193-21-1

4,6-dichloropyrimidine

(E)-3-methoxy-2-(2-hydroxyphenyl)-acrylic acid methyl ester
114077-42-8

(E)-3-methoxy-2-(2-hydroxyphenyl)-acrylic acid methyl ester

(E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate
131860-97-4

(E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate

Conditions
ConditionsYield
With caesium carbonate In N,N-dimethyl-formamide at 0℃; Inert atmosphere;84%
With caesium carbonate In N,N-dimethyl-formamide at 0℃; for 4h; Inert atmosphere;84.6%
With potassium carbonate In N,N-dimethyl-formamide at 0℃; for 12h; Inert atmosphere;83.1%
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 15h;67%
2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3,3-dimethoxypropionic acid methyl ester
143230-42-6

2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3,3-dimethoxypropionic acid methyl ester

(E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate
131860-97-4

(E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate

Conditions
ConditionsYield
With toluene-4-sulfonic acid; sodium hydroxide In toluene at 80 - 90℃; for 3h;82.3%
With methanesulfonic acid In acetic anhydride at 90℃; for 2h;80%
With sodium hydrogencarbonate at 160℃; under 20 Torr; for 2h; Product distribution / selectivity;
4,6-dichloropyrimidine
1193-21-1

4,6-dichloropyrimidine

(E)-Methyl 2-[2-hydroxyphenyl]-3-methoxypropenoate

(E)-Methyl 2-[2-hydroxyphenyl]-3-methoxypropenoate

(E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate
131860-97-4

(E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide71%
With potassium carbonate In N,N-dimethyl-formamide
With potassium carbonate In N,N-dimethyl-formamide
2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3,3-dimethoxypropionic acid methyl ester
143230-42-6

2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3,3-dimethoxypropionic acid methyl ester

methane sulfonic acid

methane sulfonic acid

(E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate
131860-97-4

(E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate

Conditions
ConditionsYield
With acetic anhydride In toluene
(E)-3-methoxy-2-(2-benzyloxyphenyl)acrylic acid methyl ester
103497-78-5

(E)-3-methoxy-2-(2-benzyloxyphenyl)acrylic acid methyl ester

(E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate
131860-97-4

(E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 10% palladium on activated carbon; hydrogen / ethyl acetate / 6 h / 20 °C / 3040.2 Torr
2: caesium carbonate / N,N-dimethyl-formamide / 0 °C / Inert atmosphere
View Scheme
Multi-step reaction with 2 steps
1: palladium 10% on activated carbon; hydrogen / ethyl acetate / 12 h / 35 °C / 760.05 Torr
2: potassium carbonate / N,N-dimethyl-formamide / 12 h / 0 °C / Inert atmosphere
View Scheme
Multi-step reaction with 2 steps
1: hydrogen; 5%-palladium/activated carbon / methanol / 18 h / 20 °C / 760.05 Torr
2: potassium carbonate / N,N-dimethyl-formamide / 15 h / 20 °C
View Scheme
(Z)-3-methoxy-2-iodo-acrylic acid methyl ester
163041-47-2

(Z)-3-methoxy-2-iodo-acrylic acid methyl ester

(E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate
131860-97-4

(E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: potassium phosphate; tetrakis(triphenylphosphine) palladium(0) / 1,4-dioxane; water / 10 h / 90 °C / Inert atmosphere
2: 10% palladium on activated carbon; hydrogen / ethyl acetate / 6 h / 20 °C / 3040.2 Torr
3: caesium carbonate / N,N-dimethyl-formamide / 0 °C / Inert atmosphere
View Scheme
Multi-step reaction with 3 steps
1: potassium phosphate; tetrakis(triphenylphosphine) palladium(0) / 1,4-dioxane; water / 10 h / 90 °C / Inert atmosphere
2: palladium 10% on activated carbon; hydrogen / ethyl acetate / 12 h / 35 °C / 760.05 Torr
3: potassium carbonate / N,N-dimethyl-formamide / 12 h / 0 °C / Inert atmosphere
View Scheme
Multi-step reaction with 3 steps
1: potassium phosphate; tetrakis(triphenylphosphine) palladium(0) / 1,4-dioxane; water / 9.25 h / 20 - 90 °C / Sonication; Inert atmosphere
2: palladium 10% on activated carbon; hydrogen / ethyl acetate / 12 h / 35 °C
3: caesium carbonate / N,N-dimethyl-formamide / 4 h / 0 °C / Inert atmosphere
View Scheme
2-benzyloxyphenylboronic acid
190661-29-1

2-benzyloxyphenylboronic acid

(E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate
131860-97-4

(E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: potassium phosphate; tetrakis(triphenylphosphine) palladium(0) / 1,4-dioxane; water / 10 h / 90 °C / Inert atmosphere
2: 10% palladium on activated carbon; hydrogen / ethyl acetate / 6 h / 20 °C / 3040.2 Torr
3: caesium carbonate / N,N-dimethyl-formamide / 0 °C / Inert atmosphere
View Scheme
Multi-step reaction with 3 steps
1: potassium phosphate; tetrakis(triphenylphosphine) palladium(0) / 1,4-dioxane; water / 10 h / 90 °C / Inert atmosphere
2: palladium 10% on activated carbon; hydrogen / ethyl acetate / 12 h / 35 °C / 760.05 Torr
3: potassium carbonate / N,N-dimethyl-formamide / 12 h / 0 °C / Inert atmosphere
View Scheme
Multi-step reaction with 3 steps
1: potassium phosphate; tetrakis(triphenylphosphine) palladium(0) / 1,4-dioxane; water / 9.25 h / 20 - 90 °C / Sonication; Inert atmosphere
2: palladium 10% on activated carbon; hydrogen / ethyl acetate / 12 h / 35 °C
3: caesium carbonate / N,N-dimethyl-formamide / 4 h / 0 °C / Inert atmosphere
View Scheme
2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxyacrylic acid
478413-47-7

2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxyacrylic acid

sodium methylate
124-41-4

sodium methylate

(E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate
131860-97-4

(E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate

Conditions
ConditionsYield
In methanol
3-(α-methoxy)methylene benzofuran-2-(3H)-ketone
40800-90-6

3-(α-methoxy)methylene benzofuran-2-(3H)-ketone

(E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate
131860-97-4

(E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: sodium / 0.5 h / -10 °C
1.2: 1 h / Inert atmosphere
2.1: potassium carbonate / N,N-dimethyl-formamide / 8 h / 60 °C
3.1: methanesulfonic acid / acetic anhydride / 2 h / 90 °C
View Scheme
Multi-step reaction with 3 steps
1: 1 h / -5 - 0 °C
2: methyl 1,4-diazabicyclo<2.2.2>octane-2-carboxylate; sodium carbonate / toluene / 4 h / 20 °C
3: acetic anhydride; methanesulfonic acid / toluene / 8 h / 95 - 100 °C
View Scheme
Multi-step reaction with 3 steps
1: polyethylene glycol 600 / tetrahydrofuran / 5 - 20 °C / Inert atmosphere; Large scale
2: sodium methylate / tetrahydrofuran / 75 h / 25 °C / Large scale
3: methanesulfonic acid / toluene / 1.5 h / 85 °C / Large scale
View Scheme
2-(2-hydroxyphenyl)-3,3-dimethoxypropionic acid methyl ester
175971-61-6

2-(2-hydroxyphenyl)-3,3-dimethoxypropionic acid methyl ester

(E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate
131860-97-4

(E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: potassium carbonate / N,N-dimethyl-formamide / 8 h / 60 °C
2: methanesulfonic acid / acetic anhydride / 2 h / 90 °C
View Scheme
Multi-step reaction with 2 steps
1: sodium carbonate / toluene / 4 h / 20 °C
2: methanesulfonic acid; acetic anhydride / 6 h / 105 - 110 °C
View Scheme
Multi-step reaction with 2 steps
1: methyl 1,4-diazabicyclo<2.2.2>octane-2-carboxylate; sodium carbonate / toluene / 4 h / 20 °C
2: acetic anhydride; methanesulfonic acid / toluene / 8 h / 95 - 100 °C
View Scheme
Multi-step reaction with 2 steps
1: sodium carbonate / toluene / 4 h / 20 °C
2: acetic anhydride; methanesulfonic acid / toluene / 6 h / 105 - 110 °C
View Scheme
2-Hydroxyphenylacetic acid
614-75-5

2-Hydroxyphenylacetic acid

(E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate
131860-97-4

(E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: 2-Methylpropionic anhydride / 10 h / 100 °C
2.1: sodium / 0.5 h / -10 °C
2.2: 1 h / Inert atmosphere
3.1: potassium carbonate / N,N-dimethyl-formamide / 8 h / 60 °C
4.1: methanesulfonic acid / acetic anhydride / 2 h / 90 °C
View Scheme
Multi-step reaction with 5 steps
1.1: acetyl chloride; hydrogenchloride / 20 h / 20 °C
2.1: potassium carbonate / N,N-dimethyl-formamide / 10 h / 20 °C
3.1: sodium hydride / N,N-dimethyl-formamide / 3 h
3.2: 2 h / 20 °C
4.1: hydrogen; 5%-palladium/activated carbon / methanol / 18 h / 20 °C / 760.05 Torr
5.1: potassium carbonate / N,N-dimethyl-formamide / 15 h / 20 °C
View Scheme
Multi-step reaction with 5 steps
1: acetic anhydride / 2.5 h / 110 °C / Inert atmosphere; Large scale
2: 21 h / 110 °C / Large scale
3: polyethylene glycol 600 / tetrahydrofuran / 5 - 20 °C / Inert atmosphere; Large scale
4: sodium methylate / tetrahydrofuran / 75 h / 25 °C / Large scale
5: methanesulfonic acid / toluene / 1.5 h / 85 °C / Large scale
View Scheme
Multi-step reaction with 3 steps
1.1: acetic anhydride / 2 h / 100 °C / Inert atmosphere; Large scale
1.2: 19 h / 100 °C / Large scale
2.1: tetrahydrofuran; methanol / 72 h / 3 - 24 °C / Inert atmosphere; Large scale
3.1: methanesulfonic acid / 1 h / Heating; Large scale
View Scheme
methyl (2E)-3-methoxy-2-propenoate
5788-17-0

methyl (2E)-3-methoxy-2-propenoate

(E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate
131860-97-4

(E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: iodine; pyridine / tetrachloromethane / 72 h / 0 - 20 °C / Inert atmosphere
2: potassium phosphate; tetrakis(triphenylphosphine) palladium(0) / 1,4-dioxane; water / 10 h / 90 °C / Inert atmosphere
3: palladium 10% on activated carbon; hydrogen / ethyl acetate / 12 h / 35 °C / 760.05 Torr
4: potassium carbonate / N,N-dimethyl-formamide / 12 h / 0 °C / Inert atmosphere
View Scheme
2-bromophenyl benzyl ether
31575-75-4

2-bromophenyl benzyl ether

(E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate
131860-97-4

(E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: magnesium; iodine / tetrahydrofuran / 2 h / 47 °C / Inert atmosphere
1.2: 4 h / -30 - 20 °C / Inert atmosphere
1.3: Grignard Reaction / 0.5 h / 20 °C
2.1: potassium phosphate; tetrakis(triphenylphosphine) palladium(0) / 1,4-dioxane; water / 10 h / 90 °C / Inert atmosphere
3.1: palladium 10% on activated carbon; hydrogen / ethyl acetate / 12 h / 35 °C / 760.05 Torr
4.1: potassium carbonate / N,N-dimethyl-formamide / 12 h / 0 °C / Inert atmosphere
View Scheme
Multi-step reaction with 4 steps
1.1: magnesium; iodine / tetrahydrofuran / 0.08 h / 35 - 47 °C / Inert atmosphere
1.2: 5 h / -30 °C / pH 2
2.1: potassium phosphate; tetrakis(triphenylphosphine) palladium(0) / 1,4-dioxane; water / 9.25 h / 20 - 90 °C / Sonication; Inert atmosphere
3.1: palladium 10% on activated carbon; hydrogen / ethyl acetate / 12 h / 35 °C
4.1: caesium carbonate / N,N-dimethyl-formamide / 4 h / 0 °C / Inert atmosphere
View Scheme
2-hydroxybromobenzene
95-56-7

2-hydroxybromobenzene

(E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate
131860-97-4

(E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: potassium carbonate / N,N-dimethyl-formamide / 3.5 h / 30 °C / Inert atmosphere
2.1: magnesium; iodine / tetrahydrofuran / 2 h / 47 °C / Inert atmosphere
2.2: 4 h / -30 - 20 °C / Inert atmosphere
2.3: Grignard Reaction / 0.5 h / 20 °C
3.1: potassium phosphate; tetrakis(triphenylphosphine) palladium(0) / 1,4-dioxane; water / 10 h / 90 °C / Inert atmosphere
4.1: palladium 10% on activated carbon; hydrogen / ethyl acetate / 12 h / 35 °C / 760.05 Torr
5.1: potassium carbonate / N,N-dimethyl-formamide / 12 h / 0 °C / Inert atmosphere
View Scheme
Multi-step reaction with 5 steps
1.1: potassium carbonate / N,N-dimethyl-formamide / 3.5 h / 30 °C / Inert atmosphere
2.1: magnesium; iodine / tetrahydrofuran / 0.08 h / 35 - 47 °C / Inert atmosphere
2.2: 5 h / -30 °C / pH 2
3.1: potassium phosphate; tetrakis(triphenylphosphine) palladium(0) / 1,4-dioxane; water / 9.25 h / 20 - 90 °C / Sonication; Inert atmosphere
4.1: palladium 10% on activated carbon; hydrogen / ethyl acetate / 12 h / 35 °C
5.1: caesium carbonate / N,N-dimethyl-formamide / 4 h / 0 °C / Inert atmosphere
View Scheme
4,6-dichloropyrimidine
1193-21-1

4,6-dichloropyrimidine

3-(α-methoxy)methylene benzofuran-2-(3H)-ketone
40800-90-6

3-(α-methoxy)methylene benzofuran-2-(3H)-ketone

sodium methylate
124-41-4

sodium methylate

A

2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3,3-dimethoxypropionic acid methyl ester
143230-42-6

2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3,3-dimethoxypropionic acid methyl ester

B

(E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate
131860-97-4

(E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate

Conditions
ConditionsYield
With Methyl formate; potassium carbonate; 2-methyl-1,4-diazabicyclo [2,2,2]octane In methanol; toluene at 5 - 20℃; for 1.5h; Temperature; Reagent/catalyst; Time; Inert atmosphere; Overall yield = 92.7 %;
With trimethylamine In methanol; toluene at 5℃; for 6h; Catalytic behavior; Temperature; Reagent/catalyst;
With 3-dimethylamino-1-azabicyclo[2.2.2]octane In methanol; toluene at 5 - 15℃; for 2h;
...Expand
benzofuran-2(3H)-one
553-86-6

benzofuran-2(3H)-one

(E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate
131860-97-4

(E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: sodium hydride / N,N-dimethyl-formamide / 2 h / -10 - 0 °C
2: potassium carbonate / N,N-dimethyl-formamide / 2 h / 20 °C
3: sodium methylate / Methyl formate / 10 h / 20 - 25 °C
View Scheme
Multi-step reaction with 4 steps
1: 21 h / 110 °C / Large scale
2: polyethylene glycol 600 / tetrahydrofuran / 5 - 20 °C / Inert atmosphere; Large scale
3: sodium methylate / tetrahydrofuran / 75 h / 25 °C / Large scale
4: methanesulfonic acid / toluene / 1.5 h / 85 °C / Large scale
View Scheme
Multi-step reaction with 3 steps
1: acetic anhydride / 95 - 100 °C
2: sodium methylate / toluene / 20 - 25 °C
3: toluene-4-sulfonic acid; sodium hydroxide / toluene / 3 h / 80 - 90 °C
View Scheme
Multi-step reaction with 3 steps
1: water / 12 h / 100 °C / Autoclave
2: sodium / 1 h / 0 °C
3: sodium / 1 h / 0 °C
View Scheme
3-formylbenzofuran-2(3H)-one
40800-88-2

3-formylbenzofuran-2(3H)-one

(E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate
131860-97-4

(E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: potassium carbonate / N,N-dimethyl-formamide / 2 h / 20 °C
2: sodium methylate / Methyl formate / 10 h / 20 - 25 °C
View Scheme
4,6-dichloropyrimidine
1193-21-1

4,6-dichloropyrimidine

3-(α-methoxy)methylene benzofuran-2-(3H)-ketone
40800-90-6

3-(α-methoxy)methylene benzofuran-2-(3H)-ketone

(E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate
131860-97-4

(E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate

Conditions
ConditionsYield
With sodium methylate In Methyl formate at 20 - 25℃; for 10h;
methyl 3-methoxyprop-2-enoate
34846-90-7

methyl 3-methoxyprop-2-enoate

(E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate
131860-97-4

(E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: pyridine; iodine / tetrachloromethane / 72 h / 0 - 20 °C / Inert atmosphere
2: potassium phosphate; tetrakis(triphenylphosphine) palladium(0) / 1,4-dioxane; water / 9.25 h / 20 - 90 °C / Sonication; Inert atmosphere
3: palladium 10% on activated carbon; hydrogen / ethyl acetate / 12 h / 35 °C
4: caesium carbonate / N,N-dimethyl-formamide / 4 h / 0 °C / Inert atmosphere
View Scheme
methyl (2-hydroxyphenyl)acetate
22446-37-3

methyl (2-hydroxyphenyl)acetate

(E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate
131860-97-4

(E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: potassium carbonate / N,N-dimethyl-formamide / 10 h / 20 °C
2.1: sodium hydride / N,N-dimethyl-formamide / 3 h
2.2: 2 h / 20 °C
3.1: hydrogen; 5%-palladium/activated carbon / methanol / 18 h / 20 °C / 760.05 Torr
4.1: potassium carbonate / N,N-dimethyl-formamide / 15 h / 20 °C
View Scheme
2-benzyloxyphenylacetic acid methyl ester
40525-65-3

2-benzyloxyphenylacetic acid methyl ester

(E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate
131860-97-4

(E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: sodium hydride / N,N-dimethyl-formamide / 3 h
1.2: 2 h / 20 °C
2.1: hydrogen; 5%-palladium/activated carbon / methanol / 18 h / 20 °C / 760.05 Torr
3.1: potassium carbonate / N,N-dimethyl-formamide / 15 h / 20 °C
View Scheme
4,6-dichloropyrimidine
1193-21-1

4,6-dichloropyrimidine

3-(α-methoxy)methylene benzofuran-2-(3H)-ketone
40800-90-6

3-(α-methoxy)methylene benzofuran-2-(3H)-ketone

A

2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3,3-dimethoxypropionic acid methyl ester
143230-42-6

2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3,3-dimethoxypropionic acid methyl ester

B

(E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate
131860-97-4

(E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate

Conditions
ConditionsYield
With sodium methylate; potassium carbonate; 2-methyl-1,4-diazabicyclo [2,2,2]octane In methanol; Methyl formate; toluene at 5 - 20℃; for 1.5h; Reagent/catalyst; Temperature; Inert atmosphere; Overall yield = 92.3 %Chromat.;
...Expand
(E)-3-(α-methoxy)methylenebenzofuran-2(3H)-one
40800-90-6

(E)-3-(α-methoxy)methylenebenzofuran-2(3H)-one

(E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate
131860-97-4

(E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: methanol / 1 h / -5 - 0 °C
2: sodium carbonate / toluene / 4 h / 20 °C
3: methanesulfonic acid; acetic anhydride / 6 h / 105 - 110 °C
View Scheme
methyl 2-(2-hydroxyphenyl)-3-methoxyacrylate
125808-20-0

methyl 2-(2-hydroxyphenyl)-3-methoxyacrylate

(E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate
131860-97-4

(E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sodium methylate / tetrahydrofuran / 75 h / 25 °C / Large scale
2: methanesulfonic acid / toluene / 1.5 h / 85 °C / Large scale
View Scheme
3-(α-methoxy)methylene benzofuran-2-(3H)-ketone
40800-90-6

3-(α-methoxy)methylene benzofuran-2-(3H)-ketone

A

2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3,3-dimethoxypropionic acid methyl ester
143230-42-6

2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3,3-dimethoxypropionic acid methyl ester

B

(E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate
131860-97-4

(E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 1 h / -5 - 0 °C
2: sodium carbonate; methyl 1,4-diazabicyclo<2.2.2>octane-2-carboxylate / toluene / 2 h / 20 °C
View Scheme
(E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate
131860-97-4

(E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate

azoxystrobin
215934-32-0, 131860-33-8

azoxystrobin

Conditions
ConditionsYield
Stage #1: salicylonitrile With potassium carbonate; 1,4-diaza-bicyclo[2.2.2]octane In N,N-dimethyl-formamide at 60℃; for 0.166667h;
Stage #2: (E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate In N,N-dimethyl-formamide at 60 - 84℃; for 0.333333h; Product distribution / selectivity;		100%
Stage #1: salicylonitrile With potassium carbonate In cyclohexanone at 100℃; for 0.166667h;
Stage #2: (E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate; 1,4-diaza-bicyclo[2.2.2]octane In cyclohexanone at 100℃; for 1.66667h; Product distribution / selectivity;		96.3%
Stage #1: salicylonitrile; 1,4-diaza-bicyclo[2.2.2]octane In toluene at 70℃; for 0.5h;
Stage #2: With 1,8-diazabicyclo[5.4.0]undec-7-ene In toluene at 70 - 74℃; for 0.25h;
Stage #3: (E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate In toluene at 70℃; for 0.5h; Product distribution / selectivity;		94.7%
(E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate
131860-97-4

(E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate

salicylonitrile
611-20-1

salicylonitrile

azoxystrobin
215934-32-0, 131860-33-8

azoxystrobin

Conditions
ConditionsYield
With potassium carbonate; quinuclidine hydrochloride In 4-methyl-2-pentanone at 60 - 80℃; for 0.5h; Product distribution / selectivity;100%
With potassium carbonate; 1,4-diaza-bicyclo[2.2.2]octane In N,N-dimethyl-formamide at 48 - 65℃; for 1h; Product distribution / selectivity;98.3%
Stage #1: (E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate; salicylonitrile In N,N-dimethyl-formamide at 60℃; for 0.0833333h;
Stage #2: 1,4-diaza-bicyclo[2.2.2]octane In N,N-dimethyl-formamide at 60℃; for 0.0833333h;
Stage #3: With potassium carbonate In N,N-dimethyl-formamide at 60 - 89℃; for 0.166667h; Product distribution / selectivity;		97.1%
(E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate
131860-97-4

(E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate

2-hydroxybenzonitrile potassium salt

2-hydroxybenzonitrile potassium salt

azoxystrobin
215934-32-0, 131860-33-8

azoxystrobin

Conditions
ConditionsYield
With potassium carbonate; triethylamine In water; toluene at 80℃; for 10h;96.12%
2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3,3-dimethoxypropionic acid methyl ester
143230-42-6

2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3,3-dimethoxypropionic acid methyl ester

(E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate
131860-97-4

(E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate

salicylonitrile
611-20-1

salicylonitrile

A

2-[2-[6-(2-cyanophenoxy)pyrimidin-4-yloxy]phenyl]-3,3-dimethoxypropionic acid methyl ester

2-[2-[6-(2-cyanophenoxy)pyrimidin-4-yloxy]phenyl]-3,3-dimethoxypropionic acid methyl ester

B

azoxystrobin
215934-32-0, 131860-33-8

azoxystrobin

Conditions
ConditionsYield
Stage #1: 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3,3-dimethoxypropionic acid methyl ester; (E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate; salicylonitrile With potassium carbonate In Isopropyl acetate at 60℃; for 0.166667h;
Stage #2: With 1,4-diaza-bicyclo[2.2.2]octane In Isopropyl acetate at 90℃; for 6h; Product distribution / selectivity;		A 91.45%
B 4.4%
With 1,4-diaza-bicyclo[2.2.2]octane; potassium carbonate In Isopropyl acetate for 6.5h; Product distribution / selectivity; Heating / reflux;A 82.85%
B 7.05%
With 1,4-diaza-bicyclo[2.2.2]octane; potassium carbonate In cyclohexanone at 90℃; for 2.33333 - 4h; Product distribution / selectivity;A 73%
B 18.3%
...Expand
(E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate
131860-97-4

(E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate

tert-butyl 6-(3-cyano-4-hydroxyphenyl)hexanoate
1266105-23-0

tert-butyl 6-(3-cyano-4-hydroxyphenyl)hexanoate

tert-butyl 6-(3-cyano-4-(6-(2-((E)-1-(methoxycarbonyl)-2-methoxyvinyl)phenoxy) pyrimidin-4-yloxy)phenyl)hexanoate
1266105-24-1

tert-butyl 6-(3-cyano-4-(6-(2-((E)-1-(methoxycarbonyl)-2-methoxyvinyl)phenoxy) pyrimidin-4-yloxy)phenyl)hexanoate

Conditions
ConditionsYield
With caesium carbonate In N,N-dimethyl-formamide at 85℃; for 3h; Inert atmosphere;91%
(E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate
131860-97-4

(E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate

sodium thiomethoxide
5188-07-8

sodium thiomethoxide

A

(E)-methyl 2-[2-(6-(2-cyanoanilino)pyrimidin-4-yloxy)phenyl]-3-methoxypropenoate
141190-17-2

(E)-methyl 2-[2-(6-(2-cyanoanilino)pyrimidin-4-yloxy)phenyl]-3-methoxypropenoate

B

(E)-methyl 2-[2-(6-methylthiopyrimidin-4-yloxy)phenyl]-3-methoxypropenoate
131860-99-6

(E)-methyl 2-[2-(6-methylthiopyrimidin-4-yloxy)phenyl]-3-methoxypropenoate

Conditions
ConditionsYield
tetrabutylammomium bromide In chloroform; waterA 89%
B n/a
...Expand
(E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate
131860-97-4

(E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate

ethyl 2-(2-hydroxyphenyl)acetate
41873-65-8

ethyl 2-(2-hydroxyphenyl)acetate

C25H24N2O7

C25H24N2O7

Conditions
ConditionsYield
With 1,4-diaza-bicyclo[2.2.2]octane; potassium carbonate In N,N-dimethyl-formamide at 80℃; for 2h; Inert atmosphere;89%
(E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate
131860-97-4

(E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate

toluene-3-thiol
108-40-7

toluene-3-thiol

C22H20N2O4S

C22H20N2O4S

Conditions
ConditionsYield
With 1,4-diaza-bicyclo[2.2.2]octane; potassium carbonate In N,N-dimethyl-formamide at 80℃; for 2h; Inert atmosphere;88%
(E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate
131860-97-4

(E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate

2-thiocresol
137-06-4

2-thiocresol

C22H20N2O4S

C22H20N2O4S

Conditions
ConditionsYield
With 1,4-diaza-bicyclo[2.2.2]octane; potassium carbonate In N,N-dimethyl-formamide at 80℃; for 2h; Inert atmosphere;85%
(E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate
131860-97-4

(E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate

ortho-cresol
95-48-7

ortho-cresol

C22H20N2O5

C22H20N2O5

Conditions
ConditionsYield
With 1,4-diaza-bicyclo[2.2.2]octane; potassium carbonate In N,N-dimethyl-formamide at 80℃; for 2h; Inert atmosphere;85%
(E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate
131860-97-4

(E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate

para-thiocresol
106-45-6

para-thiocresol

C22H20N2O4S

C22H20N2O4S

Conditions
ConditionsYield
With 1,4-diaza-bicyclo[2.2.2]octane; potassium carbonate In N,N-dimethyl-formamide at 80℃; for 2h; Inert atmosphere;82%
(E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate
131860-97-4

(E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate

methyl salicylate
119-36-8

methyl salicylate

C23H20N2O7

C23H20N2O7

Conditions
ConditionsYield
With 1,4-diaza-bicyclo[2.2.2]octane; potassium carbonate In N,N-dimethyl-formamide at 80℃; for 2h; Inert atmosphere;82%
(E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate
131860-97-4

(E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate

2-hydroxybenzonitrile sodium salt
74255-21-3

2-hydroxybenzonitrile sodium salt

azoxystrobin
215934-32-0, 131860-33-8

azoxystrobin

Conditions
ConditionsYield
With silica gel immobilized triethylene diamine catalyst 2 In toluene at 80 - 85℃; for 5h;82%
(E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate
131860-97-4

(E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate

4-hydroxybenzotrifluoride
402-45-9

4-hydroxybenzotrifluoride

C22H17F3N2O5

C22H17F3N2O5

Conditions
ConditionsYield
With 1,4-diaza-bicyclo[2.2.2]octane; potassium carbonate In N,N-dimethyl-formamide at 80℃; for 2h; Inert atmosphere;81%
(E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate
131860-97-4

(E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate

phenol
108-95-2

phenol

(E)-methyl 3-methoxy-2-(2-(6-phenoxypyrimidin-4-yloxy)phenyl)acrylate
131860-27-0

(E)-methyl 3-methoxy-2-(2-(6-phenoxypyrimidin-4-yloxy)phenyl)acrylate

Conditions
ConditionsYield
With caesium carbonate In N,N-dimethyl-formamide at 85℃; for 3h;80%
(E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate
131860-97-4

(E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate

1-(4-chlorophenyl)-1H-pyrazol-4-ol
77458-30-1

1-(4-chlorophenyl)-1H-pyrazol-4-ol

C24H19ClN4O5

C24H19ClN4O5

Conditions
ConditionsYield
With 1,4-diaza-bicyclo[2.2.2]octane; potassium carbonate In N,N-dimethyl-formamide at 80℃; for 2h; Inert atmosphere;79%
(E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate
131860-97-4

(E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate

3-Trifluoromethylphenol
98-17-9

3-Trifluoromethylphenol

C22H17F3N2O5

C22H17F3N2O5

Conditions
ConditionsYield
With 1,4-diaza-bicyclo[2.2.2]octane; potassium carbonate In N,N-dimethyl-formamide at 80℃; for 2h; Inert atmosphere;76%
(E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate
131860-97-4

(E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate

salicylonitrile
611-20-1

salicylonitrile

azoxystrobin
215934-32-0, 131860-33-8

azoxystrobin

2-hydroxybenzonitrile potassium salt

2-hydroxybenzonitrile potassium salt

Conditions
ConditionsYield
With potassium carbonate In water75.6%
With potassium carbonate In water70.8%
With potassium hydroxide In water61.5%
...Expand
2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3,3-dimethoxypropionic acid methyl ester
143230-42-6

2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3,3-dimethoxypropionic acid methyl ester

(E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate
131860-97-4

(E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate

2-hydroxybenzonitrile potassium salt

2-hydroxybenzonitrile potassium salt

A

2-[2-[6-(2-cyanophenoxy)pyrimidin-4-yloxy]phenyl]-3,3-dimethoxypropionic acid methyl ester

2-[2-[6-(2-cyanophenoxy)pyrimidin-4-yloxy]phenyl]-3,3-dimethoxypropionic acid methyl ester

B

azoxystrobin
215934-32-0, 131860-33-8

azoxystrobin

Conditions
ConditionsYield
Stage #1: 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3,3-dimethoxypropionic acid methyl ester; (E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate; 2-hydroxybenzonitrile potassium salt With potassium carbonate In Isopropyl acetate; water at 50℃;
Stage #2: With 1,4-diaza-bicyclo[2.2.2]octane In Isopropyl acetate; water for 3.75 - 5h; Product distribution / selectivity; Heating / reflux;		A 72.6%
B 15.4%
Stage #1: 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3,3-dimethoxypropionic acid methyl ester; (E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate With 1,4-diaza-bicyclo[2.2.2]octane; potassium carbonate In Isopropyl acetate; water at 50℃;
Stage #2: 2-hydroxybenzonitrile potassium salt In Isopropyl acetate; water for 4.33333h; Product distribution / selectivity; Heating / reflux;		A 68%
B 12.4%
...Expand
4,5-dichloropyrimidine
6554-61-6

4,5-dichloropyrimidine

(E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate
131860-97-4

(E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate

(E)-Methyl 2-[2-hydroxyphenyl]-3-methoxypropenoate

(E)-Methyl 2-[2-hydroxyphenyl]-3-methoxypropenoate

2-chloro-3-hydroxypyridine
6636-78-8

2-chloro-3-hydroxypyridine

(E)-methyl 2-[2-(6-(2-chloropyrid-3-yloxy)pyrimidin-4-yloxy)phenyl]-3-methoxypropenoate
133001-57-7

(E)-methyl 2-[2-(6-(2-chloropyrid-3-yloxy)pyrimidin-4-yloxy)phenyl]-3-methoxypropenoate

Conditions
ConditionsYield
With potassium carbonate; copper(I) chloride In N,N-dimethyl-formamide70%
...Expand
methanol
67-56-1

methanol

(E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate
131860-97-4

(E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate

C16H16N2O5

C16H16N2O5

Conditions
ConditionsYield
With 1,4-diaza-bicyclo[2.2.2]octane; potassium carbonate In N,N-dimethyl-formamide at 80℃; for 2h; Inert atmosphere;69%
(E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate
131860-97-4

(E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate

3-[(4-hydroxyphenyl)imino]-5-methyl-1-propylindolin-2-one

3-[(4-hydroxyphenyl)imino]-5-methyl-1-propylindolin-2-one

(E)-methyl 3-methoxy-2-(2-((6-(4-((5-methyl-2-oxo-1-propylindolin-3-ylidene)amino)phenoxy)pyrimidin-4-yl)oxy)phenyl)acrylate

(E)-methyl 3-methoxy-2-(2-((6-(4-((5-methyl-2-oxo-1-propylindolin-3-ylidene)amino)phenoxy)pyrimidin-4-yl)oxy)phenyl)acrylate

Conditions
ConditionsYield
Stage #1: 3-[(4-hydroxyphenyl)imino]-5-methyl-1-propylindolin-2-one With potassium carbonate In N,N-dimethyl-formamide at 70℃; for 0.5h;
Stage #2: (E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate In N,N-dimethyl-formamide at 90℃;		69%

Methyl (E)-2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxyacrylate Specification

This chemical is called Methyl (E)-2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxyacrylate, and it can also be named as benzeneacetic acid, 2-[(6-chloro-4-pyrimidinyl)oxy]-α-(methoxymethylene)-, methyl ester, (alphaE)-. With the molecular formula of C15H13ClN2O4, its molecular weight is 320.73. The CAS registry number of this chemical is 131860-97-4.

Other characteristics of the Methyl (E)-2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxyacrylate can be summarised as followings: (1)ACD/LogP: 3.78; (2)# of Rule of 5 Violations: 0 ; (3)#H bond acceptors: 6; (4)#H bond donors: 0; (5)#Freely Rotating Bonds: 6; (6)Polar Surface Area: 70.54 Å2; (7)Index of Refraction: 1.574; (8)Molar Refractivity: 81.092 cm3; (9)Molar Volume: 245.61 cm3; (10)Polarizability: 32.147×10-24cm3; (11)Surface Tension: 49.001 dyne/cm; (12)Density: 1.305 g/cm3; (13)Flash Point: 237.612 °C; (14)Enthalpy of Vaporization: 73.161 kJ/mol; (15)Boiling Point: 469.279 °C at 760 mmHg; (16)Vapour Pressure: 0 mmHg at 25°C.

You can still convert the following datas into molecular structure: 
1.SMILES: O=C(OC)C(\c2c(Oc1ncnc(Cl)c1)cccc2)=C\OC
2.InChI: InChI=1/C15H13ClN2O4/c1-20-8-11(15(19)21-2)10-5-3-4-6-12(10)22-14-7-13(16)17-9-18-14/h3-9H,1-2H3/b11-8+
3.InChIKey: YRYZZSRRDCTETP-DHZHZOJOBH
4.Std. InChI: InChI=1S/C15H13ClN2O4/c1-20-8-11(15(19)21-2)10-5-3-4-6-12(10)22-14-7-13(16)17-9-18-14/h3-9H,1-2H3/b11-8+
5.Std. InChIKey: YRYZZSRRDCTETP-DHZHZOJOSA-N

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