2-Chloro-4,6-dimethoxypyrimidine supplier

Name
2-Chloro-4,6-dimethoxypyrimidine
EINECS 603-561-5
CAS No. 13223-25-1
Article Data6
CAS DataBase
Density 1.285 g/cm³
Solubility Insoluble in water, soluble in toluene, isopropyl alcohol
Melting Point 100-105 °C
Formula C₆H₇ClN₂O₂
Boiling Point 317.1 °C at 760 mmHg
Molecular Weight 174.587
Flash Point 145.6 °C
Transport Information
Appearance white powder
Safety 26
Risk Codes 22-36-36/37/38
Molecular Structure
Hazard Symbols Xn,Xi
Synonyms 4,6-Dimethoxy-2-chloropyrimidine;AC1NP78R;61336_ALDRICH;AC1Q49B7;61336_FLUKA;
PSA 44.24000
LogP 1.14720

Synthetic route

: methyl 3-amino-3-methoxy-N-nitrile-2-propionamidine

: 13223-25-1
2-chloro-4,6-dimethoxypyrimidine

Conditions

Conditions	Yield
With hydrogenchloride In methanol at 5℃; for 2h; Temperature;	82.1%

: 36315-01-2
4,6-dimethoxy-2-aminopyrimidine

: 13223-25-1
2-chloro-4,6-dimethoxypyrimidine

Conditions

Conditions	Yield
With hydrogenchloride; sodium hydroxide; sodium nitrite In water; ethyl acetate	29.9%
With hydrogenchloride; zinc(II) chloride; sodium nitrite Chlorination;

: 13223-25-1
2-chloro-4,6-dimethoxypyrimidine

: 478010-54-7
2-chloro-4,6-dimethoxy-5-nitro-pyrimidine

Conditions

Conditions	Yield
With trifluoromethylsulfonic anhydride; tetramethylammonium nitrate In dichloromethane at 20℃; for 38h;	98%
Stage #1: 2-chloro-4,6-dimethoxypyrimidine With trifluoromethylsulfonic anhydride; tetramethylammonium nitrate In dichloromethane at 0 - 20℃; for 50.75h; Stage #2: With sodium hydrogencarbonate In dichloromethane; water	97%
With nitric acid; trifluoroacetic anhydride In dichloromethane at 20℃;	97%

: 637-44-5
phenylpropyolic acid

: 13223-25-1
2-chloro-4,6-dimethoxypyrimidine

: 329206-02-2
4,6-dimethoxy-2-(phenylethynyl)pyrimidine

Conditions

Conditions	Yield
With bis[dicyclohexyl(2,4,6-triisopropyl-[1,1':3',1''-terphenyl]-2-yl)phosphane]palladium(II) dichloride; caesium carbonate In tetrahydrofuran at 80℃; for 10h;	98%

: 92-54-6
4-phenyl-1-piperazine

: 13223-25-1
2-chloro-4,6-dimethoxypyrimidine

: 4,6-dimethoxy-2-(4-phenyl-piperazin-1-yl)-pyrimidine

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In isopropyl alcohol at 160℃; for 0.0833333h; Irradiation;	97%

: 98437-24-2
benzofuran-2-boronic acid

: 13223-25-1
2-chloro-4,6-dimethoxypyrimidine

: 1251914-08-5
2-(benzofuran-2-yl)-4,6-dimethoxypyrimidine

Conditions

Conditions	Yield
With (η3-indenyl)Pd(XPhos)(OTf); potassium carbonate In tetrahydrofuran; methanol at 40℃; for 1h; Suzuki-Miyaura Coupling; Glovebox; Sealed tube; Cooling with ethanol-dry ice;	97%
With potassium phosphate; chloro(2-dicyclohexylphosphino-2’,4’,6’-triisopropyl-1,1‘-biphenyl)[2-(2’-amino-1,1‘-biphenyl’)]palladium(II) In tetrahydrofuran; water at 40℃; for 0.5h; Suzuki-Miyaura cross-coupling; Inert atmosphere;	96%
With C46H64ClPPd; potassium carbonate In tetrahydrofuran; methanol at 40℃; for 1h; Reagent/catalyst; Suzuki-Miyaura Coupling; Inert atmosphere;	95%
With [(η3-1-tBu-indenyl)Pd(1,3-bis(2,6-diisopropylphenyl)-1,3-dihydro-2H-imidazol-2-ylidene)(Cl)]; potassium carbonate In tetrahydrofuran; methanol at 20℃; for 3h; Reagent/catalyst; Time; Suzuki-Miyaura Coupling; Inert atmosphere;

: 13223-25-1
2-chloro-4,6-dimethoxypyrimidine

: 36315-01-2
4,6-dimethoxy-2-aminopyrimidine

Conditions

Conditions	Yield
With ammonia In tetrahydrofuran; water at 100 - 110℃; for 4h; Solvent; Autoclave; Large scale;	96.3%
With dicyclohexyl(2',4',6'-triisopropyl-5-methoxy-3,4,6-trimethyl-[1,1'-biphenyl]-2-yl)phosphine; C50H70NO4PPdS; C50H70NO4PPdS; dicyclohexyl(2',4',6'-triisopropyl-4-methoxy-3,5,6-trimethyl-[1,1'-biphenyl]-2-yl)phosphine; ammonia; sodium t-butanolate In 1,4-dioxane at 50℃; for 24h; Reagent/catalyst; Inert atmosphere;	80%
Multi-step reaction with 2 steps 1: potassium carbonate / 1,4-dioxane / 96 h / Reflux 2: methanol; palladium(II) hydroxide / 48 h / 20 °C View Scheme
Multi-step reaction with 2 steps 1: potassium carbonate / 1,4-dioxane / 96 h / Reflux 2: hydrogen; palladium(II) hydroxide / methanol / 48 h / 20 °C / 760.05 Torr View Scheme

: 135884-31-0
N-boc-2-pyrroleboronic acid

: 13223-25-1
2-chloro-4,6-dimethoxypyrimidine

: C15H19N3O4

Conditions

Conditions	Yield
With O4P(3-)3K(1+)5H2O; tris(1-adamantyl)phosphine; C28H26N2O8Pd2S2 In tetrahydrofuran; butan-1-ol at 20℃; for 5h; Suzuki-Miyaura Coupling; Inert atmosphere; Schlenk technique;	96%
With O4P(3-)3K(1+)5H2O; tris(1-adamantyl)phosphine; {2-[((acetyl-κO)amino)phenyl-κC](tri-1-adamantylphosphine)palladium}(p-toluenesulfonate) In tetrahydrofuran; butan-1-ol at 20℃; for 5h; Suzuki-Miyaura Coupling;	96%

: 13223-25-1
2-chloro-4,6-dimethoxypyrimidine

: 5188-07-8
sodium thiomethoxide

: 90905-46-7
4,6-dimethoxy-2-(methylsulfanyl)pyrimidine

Conditions

Conditions	Yield
In methanol at 45 - 50℃; for 2h;	95.6%

: 109-01-3
1-methyl-piperazine

: 13223-25-1
2-chloro-4,6-dimethoxypyrimidine

: 871365-06-9
4,6-dimethoxy-2-(4-methylpiperazin-1-yl)pyrimidine

Conditions

Conditions	Yield
In N,N-dimethyl-formamide at 90℃; for 2.5h; Inert atmosphere;	95%
In N,N-dimethyl-formamide at 90℃; for 2.5h; Inert atmosphere;	95%

: 100124-06-9
4-dibenzofurylboronic acid

: 13223-25-1
2-chloro-4,6-dimethoxypyrimidine

: 1334531-07-5
2-(dibenzo[b,d]furan-4-yl)-4,6-dimethoxypyrimidine

Conditions

Conditions	Yield
With potassium phosphate; chloro(2-dicyclohexylphosphino-2’,4’,6’-triisopropyl-1,1‘-biphenyl)[2-(2’-amino-1,1‘-biphenyl’)]palladium(II); tetrabutylammomium bromide In 1-methyl-pyrrolidin-2-one; water; toluene at 90℃; Suzuki-Miyaura cross-coupling; Continuous flow reactor; Inert atmosphere;	94%

: 955397-70-3
4-(2-aminophenyl)-5,6-dihydropyridine-1(2H)-carboxylic acid tert-butyl ester

: 13223-25-1
2-chloro-4,6-dimethoxypyrimidine

: C22H28N4O4

Conditions

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate In toluene at 120℃; for 12h; Inert atmosphere;	94%

: 13223-25-1
2-chloro-4,6-dimethoxypyrimidine

: 2-chloro-5-hydroxy-4,6-dimethoxypyrimidine

Conditions

Conditions	Yield
Stage #1: 2-chloro-4,6-dimethoxypyrimidine With lithium diisopropyl amide In tetrahydrofuran; n-heptane; ethylbenzene at -78℃; Stage #2: With tert.-butylhydroperoxide; n-butyllithium In tetrahydrofuran; decane; n-heptane; ethylbenzene at -78 - 0℃; for 4h; Stage #3: With hydrogenchloride In tetrahydrofuran; decane; n-heptane; ethylbenzene; water pH=7;	93.4%
Stage #1: 2-chloro-4,6-dimethoxypyrimidine With lithium diisopropyl amide In tetrahydrofuran; n-heptane; ethylbenzene at -78℃; Inert atmosphere; Stage #2: With tert.-butylhydroperoxide; n-butyllithium In tetrahydrofuran; decane; hexane; n-heptane; ethylbenzene at -78 - 0℃; Inert atmosphere;	93.4%

: 100-46-9
benzylamine

: 13223-25-1
2-chloro-4,6-dimethoxypyrimidine

: N-benzyl-2-amino-4,6-dimethoxypyrimidine

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In isopropyl alcohol at 160℃; for 0.666667h; Irradiation;	93%
With triethylamine In isopropyl alcohol at 120℃; for 12h; Green chemistry;	90%
With potassium carbonate In 1,4-dioxane for 96h; Reflux;	87%
With potassium carbonate In 1,4-dioxane for 96h; Reflux;	87%

: 917-61-3
sodium isocyanate

: 13223-25-1
2-chloro-4,6-dimethoxypyrimidine

: 75-65-0
tert-butyl alcohol

: tert-butyl (4,6-dimethoxypyrimidin-2-yl)carbamate

Conditions

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); t-BuBrettPhos; triethylamine at 110℃; for 16h; Inert atmosphere;	93%

...Expand

: 110-91-8
morpholine

: 13223-25-1
2-chloro-4,6-dimethoxypyrimidine

: 1568908-87-1
4,6-dimethoxy-2-(morpholin-4-yl)pyrimidine

Conditions

Conditions	Yield
In N,N-dimethyl-formamide at 90℃; for 2.5h; Inert atmosphere;	93%
With triethylamine In isopropyl alcohol at 120℃; for 12h; Green chemistry;	84%

: 13223-25-1
2-chloro-4,6-dimethoxypyrimidine

: 135217-37-7
7-mercapto-3-methyl-3H-isobenzofuran-1-one

: 135186-78-6
7-[(4,6-dimethoxy-pyrimidin-2-yl)thio]-3-methyl-phthalide

Conditions

Conditions	Yield
With potassium carbonate; triphenylphosphine In acetonitrile at 55℃; for 23h;	91.1%

: 931-49-7
1-ethenylcyclohexene

: 13223-25-1
2-chloro-4,6-dimethoxypyrimidine

: 1418137-10-6
2-(cyclohexenylethynyl)-4,6-dimethoxypyrimidine

Conditions

Conditions	Yield
With bis[di-tert-butyl(4-dimethylaminophenyl)phosphine]palladium(0); caesium carbonate In acetonitrile at 90℃; for 5h; Sonogashira Cross-Coupling; Inert atmosphere;	91%
With potassium phosphate; bis[dicyclohexyl(2,4,6-triisopropyl-[1,1':3',1''-terphenyl]-2-yl)phosphane]palladium(II) dichloride In acetonitrile at 90℃; for 6h; Sonogashira Cross-Coupling;	75%

: 19981-17-0, 20611-81-8, 123092-13-7, 17292-62-5
sodium cyanamide

: 13223-25-1
2-chloro-4,6-dimethoxypyrimidine

: 2-cyanamino-4,6-dimethoxypyrimidine

Conditions

Conditions	Yield
With 1-methyl-pyrrolidin-2-one at 20℃; Inert atmosphere;	91%

: 67-56-1
methanol

: 201230-82-2
carbon monoxide

: 13223-25-1
2-chloro-4,6-dimethoxypyrimidine

: methyl 4,6-dimethoxypyrimidine-2-carboxylate

Conditions

Conditions	Yield
With 1,1'-bis-(diphenylphosphino)ferrocene; palladium diacetate; sodium acetate at 165℃; under 11250.9 Torr; for 2h; Product distribution; various reaction conditions;	90%
With 1,1'-bis-(diphenylphosphino)ferrocene; palladium diacetate; sodium acetate at 165℃; under 11250.9 Torr; for 2h;	90%

...Expand

: 104217-48-3
3-hydroxy-pyridine-2-carbaldehyde-diethylacetal

: 13223-25-1
2-chloro-4,6-dimethoxypyrimidine

A: 136429-20-4
3-(4,6-dimethoxy-2-pyrimidinyloxy)-2-pyridinecarboxaldehyde diethylacetal

B: 3-(4,6-dimethoxy-2-pyrimidinyloxy)-2-pyridinecarboxaldehyde diethylacetate

Conditions

Conditions	Yield
In water	A n/a B 90%

...Expand

: 350595-57-2
(S)-3-methylmorpholine

: 13223-25-1
2-chloro-4,6-dimethoxypyrimidine

: (3S)-4-(4,6-dimethoxypyrimidin-2-yl)-3-methylmorpholine

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dimethyl sulfoxide at 100℃; for 22h; Sealed tube;	90%
With N-ethyl-N,N-diisopropylamine In dimethyl sulfoxide at 100℃; for 22h;	90%
With N-ethyl-N,N-diisopropylamine In dimethyl sulfoxide at 100℃; for 22h; Sealed tube;	90%

: 927-74-2
1-butyn-4-ol

: 13223-25-1
2-chloro-4,6-dimethoxypyrimidine

: 2-(but-3-ynyloxy)-4,6-dimethoxypyrimidine

Conditions

Conditions	Yield
Stage #1: 3-Butyn-1-ol; 2-chloro-4,6-dimethoxypyrimidine With sodium hydride In tetrahydrofuran at 0℃; for 0.5h; Inert atmosphere; Stage #2: In tetrahydrofuran at 20℃; for 17h; Inert atmosphere;	90%

: 371-40-4
4-fluoroaniline

: 13223-25-1
2-chloro-4,6-dimethoxypyrimidine

: 1627898-12-7
2-[(4-fluorophenyl)amino]-4,6-dimethoxypyrimidine

Conditions

Conditions	Yield
With Pd(PAd3)(4-FC6H4)Br; triethylamine In water; toluene at 100℃; for 16h; Inert atmosphere; Glovebox;	90%

: 771-99-3
4-phenylpiperidine

: 13223-25-1
2-chloro-4,6-dimethoxypyrimidine

: 4,6-dimethoxy-2-(4-phenylpiperidine-1-yl)pyrimidine

Conditions

Conditions	Yield
With triethylamine In isopropyl alcohol at 120℃; for 12h; Green chemistry;	88%

: 64-17-5
ethanol

: 201230-82-2
carbon monoxide

: 13223-25-1
2-chloro-4,6-dimethoxypyrimidine

: 128276-49-3
ethyl 4,6-dimethoxy-2-pyrimidinecarboxylate

Conditions

Conditions	Yield
With 1,1'-bis-(diphenylphosphino)ferrocene; palladium diacetate; sodium acetate at 160℃; under 11250.9 Torr; for 2.5h;	87%

...Expand

: 13223-25-1
2-chloro-4,6-dimethoxypyrimidine

: 1269417-63-1
2-iodo-4,6-dimethoxypyrimidine

Conditions

Conditions	Yield
With hydrogen iodide at 0 - 20℃; for 4h;	87%

: 123-75-1
pyrrolidine

: 13223-25-1
2-chloro-4,6-dimethoxypyrimidine

: 1622148-58-6
4,6-dimethoxy-2-(pyrrolidine-1-yl)pyrimidine

Conditions

Conditions	Yield
With triethylamine In isopropyl alcohol at 120℃; for 12h; Green chemistry;	87%
Stage #1: pyrrolidine With sodium hydride In tetrahydrofuran for 0.5h; Reflux; Stage #2: 2-chloro-4,6-dimethoxypyrimidine In tetrahydrofuran for 48h; Reflux;	71%

: 120-72-9
indole

: 13223-25-1
2-chloro-4,6-dimethoxypyrimidine

: 1-(4,6-dimethoxypyrimidin-2-yl)-1H-indole

Conditions

Conditions	Yield
With C45H39BrNiOP2; lithium tert-butoxide; phenylboronic acid In toluene at 110℃; for 16h; Inert atmosphere; Glovebox; Sealed tube;	87%

: 122-39-4
diphenylamine

: 13223-25-1
2-chloro-4,6-dimethoxypyrimidine

: 1501945-27-2
4,6-dimethoxy-N,N-diphenylpyrimidin-2-amine

Conditions

Conditions	Yield
With 1,1'-bis-(diphenylphosphino)ferrocene; cis-[1,1'-bis(diphenylphosphino)ferrocene](2-methylphenyl)nickel(II) chloride; acetonitrile; lithium tert-butoxide at 130℃; for 16h; Inert atmosphere;	86%

: 107-15-3
ethylenediamine

: 13223-25-1
2-chloro-4,6-dimethoxypyrimidine

: N-(1-aminoethan-2-yl)-2-amino-4,6-dimethoxypyrimidine

Conditions

Conditions	Yield
With triethylamine In isopropyl alcohol at 120℃; for 12h; Green chemistry;	86%

: 76350-90-8
(2-methyl-[1,1'-biphenyl]-3-yl)methanol

: 13223-25-1
2-chloro-4,6-dimethoxypyrimidine

: 4,6-dimethoxy-2-((2-methyl-[1,1'-biphenyl]-3-yl)methoxy)pyrimidine

Conditions

Conditions	Yield
Stage #1: (2-methyl[1,1'-biphenyl]-3-yl)methanol With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃; for 0.5h; Stage #2: 2-chloro-4,6-dimethoxypyrimidine In N,N-dimethyl-formamide at 0 - 20℃; for 2h;	83%

2-Chloro-4,6-dimethoxypyrimidine Specification

The 2-Chloro-4,6-dimethoxypyrimidine with CAS registry number of 13223-25-1 is also known as Pyrimidine,2-chloro-4,6-dimethoxy-. The IUPAC name and product name are the same. It belongs to product categories of Pyrimidine; Pyrimidines; Building Blocks; Heterocyclic Building Blocks; Dimethoxy pyrimidines. In addition, the formula is C₆H₇ClN₂O₂ and the molecular weight is 174.59.

Physical properties about 2-Chloro-4,6-dimethoxypyrimidine are: (1)ACD/LogP: 0.07; (2)ACD/LogD (pH 5.5): 0.07; (3)ACD/LogD (pH 7.4): 0.07; (4)ACD/BCF (pH 5.5): 1; (5)ACD/BCF (pH 7.4): 1; (6)ACD/KOC (pH 5.5): 26.04; (7)ACD/KOC (pH 7.4): 26.04; (8)#H bond acceptors: 4; (9)#Freely Rotating Bonds: 2; (10)Index of Refraction: 1.51; (11)Molar Refractivity: 40.68 cm³; (12)Molar Volume: 135.8 cm³; (13)Surface Tension: 41.5 dyne/cm; (14)Density: 1.285 g/cm³; (15)Flash Point: 145.6 °C; (16)Enthalpy of Vaporization: 53.63 kJ/mol; (17)Boiling Point: 317.1 °C at 760 mmHg; (18)Vapour Pressure: 0.00073 mmHg at 25 °C.

Preparation of 2-Chloro-4,6-dimethoxypyrimidine: it is prepared by reaction of malononitrile. 3-Amino-3-methoxy-N-cyano-2-C amidine intermediate is received and dispersed in toluene. Then dry hydrogen chloride is passed at the temperature of 0 °C under stirring for 2 hours. After reaction, adding water to the mixture and the water layer is extracted with toluene. At last, product is obtained by combining toluene solution, vacuum steam and drying.

Uses of 2-Chloro-4,6-dimethoxypyrimidine: it is used as pesticide intermediate and used to produce 7-(4,6-dimethoxy-pyrimidin-2-ylsulfanyl)-3-methyl-3H-isobenzofuran-1-one by reaction with 7-mercapto-3-methyl-3H-isobenzofuran-1-one. The reaction occurs with reagents K₂CO₃, triphenylphosphine and solvent acetonitrile at the temperature of 55 °C for 23 hours. The yield is about 91.1%.

2-Chloro-4,6-dimethoxypyrimidine is used to produce 7-(4,6-dimethoxy-pyrimidin-2-ylsulfanyl)-3-methyl-3H-isobenzofuran-1-one by reaction with 7-mercapto-3-methyl-3H-isobenzofuran-1-one.

When you are using this chemical, please be cautious about it. As a chemical, it is irritating to eyes, respiratory system and skin. Besides, it is harmful if swallowed. If contact with eyes accidently, rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
1. Canonical SMILES: COC1=CC(=NC(=N1)Cl)OC
2. InChI: InChI=1S/C6H7ClN2O2/c1-10-4-3-5(11-2)9-6(7)8-4/h3H,1-2H3
3. InChIKey: PBEKEFWBLFBSGQ-UHFFFAOYSA-N

Product Name

2-Chloro-4,6-dimethoxypyrimidine

Synthetic route

2-Chloro-4,6-dimethoxypyrimidine Specification

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