Product Name

  • Name

    2-Methylthio-4-pyrimidinol

  • EINECS 227-274-6
  • CAS No. 5751-20-2
  • Article Data31
  • CAS DataBase
  • Density 1.35 g/cm3
  • Solubility
  • Melting Point 200.0 to 204.0 °C
  • Formula C5H6N2OS
  • Boiling Point 301.2 °C at 760 mmHg
  • Molecular Weight 142.181
  • Flash Point 136 °C
  • Transport Information
  • Appearance
  • Safety 26-39
  • Risk Codes 22-37/38-41
  • Molecular Structure Molecular Structure of 5751-20-2 (2-Methylthio-4-pyrimidinol)
  • Hazard Symbols Xn
  • Synonyms 4(1H)-Pyrimidinone,2-(methylthio)- (8CI,9CI);4-Pyrimidinol, 2-(methylthio)- (6CI,7CI);2-(Methylthio)-4(1H)-pyrimidinone;2-(Methylthio)-4(3H)-pyrimidinone;2-(Methylthio)-4-pyrimidinone;2-(Methylthio)-4-pyrimidone;2-(Methylthio)pyrimidine-4(3H)-one;2-Methylsulfanyl-3H-pyrimidin-4-one;2-Methylsulfanylpyrimidin-4-ol;2-Methylthio-3H-pyrimidin-4-one;2-Methylthio-4-hydroxypyrimidine;2-Methylthiouracil;4-Hydroxy-2-(methylthio)pyrimidine;NSC 125339;
  • PSA 71.05000
  • LogP 0.49180

Synthetic route

2-thiouracil
141-90-2

2-thiouracil

methyl iodide
74-88-4

methyl iodide

2-Methylthiouracil
5751-20-2

2-Methylthiouracil

Conditions
ConditionsYield
Stage #1: 2-thiouracil; methyl iodide With sodium hydroxide In water at 20℃; for 16h;
Stage #2: With acetic acid In water		100%
Stage #1: 2-thiouracil With sodium hydroxide In water at 60 - 70℃;
Stage #2: methyl iodide In ethanol; water at 30 - 60℃; for 0.333333h;
Stage #3: With acetic acid In ethanol; water at 20℃;		100%
With sodium hydroxide at 20℃; for 18h;99%
n-propyl formylacetate

n-propyl formylacetate

carbamimidothioic acid methyl ester
2986-19-8

carbamimidothioic acid methyl ester

2-Methylthiouracil
5751-20-2

2-Methylthiouracil

Conditions
ConditionsYield
In isopropyl alcohol at 35℃;97%
methyl 3-oxopropionate
63857-17-0

methyl 3-oxopropionate

carbamimidothioic acid methyl ester
2986-19-8

carbamimidothioic acid methyl ester

2-Methylthiouracil
5751-20-2

2-Methylthiouracil

Conditions
ConditionsYield
In ethanol at 10℃;96%
3-oxo-propionic acid ethyl ester
34780-29-5

3-oxo-propionic acid ethyl ester

carbamimidothioic acid methyl ester
2986-19-8

carbamimidothioic acid methyl ester

2-Methylthiouracil
5751-20-2

2-Methylthiouracil

Conditions
ConditionsYield
In methanol at 5℃; for 3h;94.9%
isopropyl formylacetate
108350-20-5

isopropyl formylacetate

carbamimidothioic acid methyl ester
2986-19-8

carbamimidothioic acid methyl ester

2-Methylthiouracil
5751-20-2

2-Methylthiouracil

Conditions
ConditionsYield
In methanol at 25℃;93%
n-butyl formylacetate

n-butyl formylacetate

carbamimidothioic acid methyl ester
2986-19-8

carbamimidothioic acid methyl ester

2-Methylthiouracil
5751-20-2

2-Methylthiouracil

Conditions
ConditionsYield
In ethanol at 25℃;93%
isobutyl formylacetate

isobutyl formylacetate

carbamimidothioic acid methyl ester
2986-19-8

carbamimidothioic acid methyl ester

2-Methylthiouracil
5751-20-2

2-Methylthiouracil

Conditions
ConditionsYield
In ethanol at 25℃;93%
3-oxo-propionic acid tert-butyl ester
108350-21-6

3-oxo-propionic acid tert-butyl ester

carbamimidothioic acid methyl ester
2986-19-8

carbamimidothioic acid methyl ester

2-Methylthiouracil
5751-20-2

2-Methylthiouracil

Conditions
ConditionsYield
In ethanol at 25℃;93%
2-thiouracil
141-90-2

2-thiouracil

carbonic acid dimethyl ester
616-38-6

carbonic acid dimethyl ester

2-Methylthiouracil
5751-20-2

2-Methylthiouracil

Conditions
ConditionsYield
With tetrabutylammomium bromide; potassium carbonate at 120℃; for 8h;93%
With tetrabutylammomium bromide; potassium carbonate In N,N-dimethyl-formamide at 120℃; for 6h;92.6%
boron dimethyl-trifluoro sulphide
353-43-5

boron dimethyl-trifluoro sulphide

2-chloropyrimidin-4(3H)-one

2-chloropyrimidin-4(3H)-one

2-Methylthiouracil
5751-20-2

2-Methylthiouracil

Conditions
ConditionsYield
In neat (no solvent) at 60℃; for 16h; Sealed tube;83%
methyl iodide
74-88-4

methyl iodide

2-Methylthiouracil
5751-20-2

2-Methylthiouracil

Conditions
ConditionsYield
Stage #1: 2-thiouracil With sodium methylate In methanol at 20℃; for 0.0833333h;
Stage #2: methyl iodide In methanol		74%
Stage #1: 2-thiouracil With sodium hydroxide In water at 20℃; for 0.333333h;
Stage #2: methyl iodide In tetrahydrofuran; water at 20℃; for 18h; Product distribution / selectivity;		60%
Stage #1: 2-thiouracil With sodium hydroxide In water at 20℃; for 0.333333h;
Stage #2: methyl iodide In tetrahydrofuran; water at 20℃; for 18h; Product distribution / selectivity;		60%
4-(dimethylamino)-2-methylsulfanyl-1,3-diazabuta-1,3-dienium iodide
344361-86-0

4-(dimethylamino)-2-methylsulfanyl-1,3-diazabuta-1,3-dienium iodide

acetyl chloride
75-36-5

acetyl chloride

2-Methylthiouracil
5751-20-2

2-Methylthiouracil

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0 - 20℃; for 3h;68%
4-hydroxy-2-mercaptopyrimidine
141-90-2

4-hydroxy-2-mercaptopyrimidine

methyl iodide
74-88-4

methyl iodide

2-Methylthiouracil
5751-20-2

2-Methylthiouracil

Conditions
ConditionsYield
With sodium hydroxide In ethanol; water at 30 - 60℃; for 0.333333h;47%
Stage #1: 4-hydroxy-2-mercaptopyrimidine With sodium methylate In methanol at 20℃; for 0.0833333h;
Stage #2: methyl iodide In methanol
trimethyl phosphite
512-56-1

trimethyl phosphite

2-thiouracil
141-90-2

2-thiouracil

A

2-Methylthiouracil
5751-20-2

2-Methylthiouracil

B

2-methylthio-3-methylpyrimidin-4(3H)-one
6327-98-6

2-methylthio-3-methylpyrimidin-4(3H)-one

C

1-methyl-2-methysulfanylpyrimidin-4(1H)-one
6330-98-9

1-methyl-2-methysulfanylpyrimidin-4(1H)-one

D

4-methoxy-2-(methylthio)pyrimidine
76541-59-8

4-methoxy-2-(methylthio)pyrimidine

Conditions
ConditionsYield
With triethylamine In N,N-dimethyl-formamide at 80℃; for 3h; Further byproducts given;A 13%
B 10%
C 35%
D 6%
...Expand
trimethyl phosphite
512-56-1

trimethyl phosphite

2-thiouracil
141-90-2

2-thiouracil

A

2-Methylthiouracil
5751-20-2

2-Methylthiouracil

B

2-methylthio-3-methylpyrimidin-4(3H)-one
6327-98-6

2-methylthio-3-methylpyrimidin-4(3H)-one

C

1-methyl-2-methysulfanylpyrimidin-4(1H)-one
6330-98-9

1-methyl-2-methysulfanylpyrimidin-4(1H)-one

D

1,3-dimethyl-2-thiouracil
1194-71-4

1,3-dimethyl-2-thiouracil

Conditions
ConditionsYield
With triethylamine In N,N-dimethyl-formamide at 80℃; for 3h; Further byproducts given;A 13%
B 10%
C 35%
D 8%
...Expand
trimethyl phosphite
512-56-1

trimethyl phosphite

2-thiouracil
141-90-2

2-thiouracil

2-Methylthiouracil
5751-20-2

2-Methylthiouracil

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 80℃; for 55h;17%
2-(methylsulfanyl)pyrimidin-4-ol
5751-20-2

2-(methylsulfanyl)pyrimidin-4-ol

2-Methylthiouracil
5751-20-2

2-Methylthiouracil

Conditions
ConditionsYield
at 226.9℃; Equilibrium constant;
4-(N-benzylcarbamoylethoxy)-2-methylthiopyrimidine
109389-01-7

4-(N-benzylcarbamoylethoxy)-2-methylthiopyrimidine

A

2-Methylthiouracil
5751-20-2

2-Methylthiouracil

B

N-benzylacrylamide
13304-62-6

N-benzylacrylamide

Conditions
ConditionsYield
With sodium hydride; paraffin In tetrahydrofuran
sodium formylacetic acid ethyl ester

sodium formylacetic acid ethyl ester

hydriodide of S-methyl-isothiourea

hydriodide of S-methyl-isothiourea

2-Methylthiouracil
5751-20-2

2-Methylthiouracil

Conditions
ConditionsYield
With sodium hydroxide
2-Methylthiouracil
5751-20-2

2-Methylthiouracil

ethyl 4-(methylamino)piperidine-1-carboxylate
73733-69-4

ethyl 4-(methylamino)piperidine-1-carboxylate

2-[(1-carbethoxy-4-piperidinyl)(methyl)amino]-1H-pyrimidin-4-one

2-[(1-carbethoxy-4-piperidinyl)(methyl)amino]-1H-pyrimidin-4-one

Conditions
ConditionsYield
for 26h; Kinetics;99.4%
2-Methylthiouracil
5751-20-2

2-Methylthiouracil

phenylboronic acid
98-80-6

phenylboronic acid

2-(methylsulfanyl)-4-phenylpyrimidine
56734-10-2

2-(methylsulfanyl)-4-phenylpyrimidine

Conditions
ConditionsYield
Stage #1: 2-Methylthiouracil With triethylamine; bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate In 1,4-dioxane at 20℃; for 2h; Inert atmosphere; Sealed tube;
Stage #2: phenylboronic acid With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In 1,4-dioxane; water at 100℃; for 4h; Suzuki coupling; Inert atmosphere; Sealed tube; chemoselective reaction;		99%
2-Methylthiouracil
5751-20-2

2-Methylthiouracil

5-iodo-4-hydroxy-6-methyl-2-methylthiopyrimidine
76510-61-7

5-iodo-4-hydroxy-6-methyl-2-methylthiopyrimidine

Conditions
ConditionsYield
With N-iodo-succinimide In chloroform at 70℃; for 2h;97%
With iodine; sodium hydroxide In water at 80℃; for 7h;87%
With sodium hydroxide; iodine In water at 80℃; for 7h;84%
With N-iodo-succinimide In chloroform at 70℃; Inert atmosphere;50%
2-Methylthiouracil
5751-20-2

2-Methylthiouracil

4-Aminobenzonitrile
873-74-5

4-Aminobenzonitrile

4-((4-hydroxypyrimidin-2-yl)amino)benzonitrile
189956-45-4

4-((4-hydroxypyrimidin-2-yl)amino)benzonitrile

Conditions
ConditionsYield
With pyridine at 110℃; for 8h; Reagent/catalyst; Temperature; Industrial scale;97%
2-Methylthiouracil
5751-20-2

2-Methylthiouracil

aniline
62-53-3

aniline

2-(phenylamino)pyrimidin-4(3H)-one
158661-55-3

2-(phenylamino)pyrimidin-4(3H)-one

Conditions
ConditionsYield
In diethylene glycol dimethyl ether Heating;96%
In diethylene glycol dimethyl ether at 170℃; for 5h;46%
2-Methylthiouracil
5751-20-2

2-Methylthiouracil

3,4,5-trimethoxyphenylboronic Acid
182163-96-8

3,4,5-trimethoxyphenylboronic Acid

2-(methylsulfanyl)-4-(3,4,5-trimethoxyphenyl)pyrimidine
1388177-39-6

2-(methylsulfanyl)-4-(3,4,5-trimethoxyphenyl)pyrimidine

Conditions
ConditionsYield
Stage #1: 2-Methylthiouracil With triethylamine; bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate In 1,4-dioxane at 20℃; for 2h; Inert atmosphere; Sealed tube;
Stage #2: 3,4,5-trimethoxyphenylboronic Acid With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In 1,4-dioxane; water at 100℃; for 4h; Suzuki coupling; Inert atmosphere; Sealed tube; chemoselective reaction;		96%
2-Methylthiouracil
5751-20-2

2-Methylthiouracil

p-toluidine
106-49-0

p-toluidine

2-<(4-methylphenyl)amino>pyrimidin-4(3H)-one

2-<(4-methylphenyl)amino>pyrimidin-4(3H)-one

Conditions
ConditionsYield
In diethylene glycol dimethyl ether Heating;94%
With Trimethylacetic acid at 130℃; Inert atmosphere;
2-Methylthiouracil
5751-20-2

2-Methylthiouracil

3-biphenyl amine
2243-47-2

3-biphenyl amine

2-(3-biphenylamino)pyrimidin-4(3H)-one
960243-28-1

2-(3-biphenylamino)pyrimidin-4(3H)-one

Conditions
ConditionsYield
In diethylene glycol dimethyl ether for 18h; Heating / reflux;92%
In diethylene glycol dimethyl ether for 18h; Heating / reflux;92%
2-Methylthiouracil
5751-20-2

2-Methylthiouracil

1-amino-3-methylbenzene
108-44-1

1-amino-3-methylbenzene

2-<(3-methylphenyl)amino>pyrimidin-4(3H)-one

2-<(3-methylphenyl)amino>pyrimidin-4(3H)-one

Conditions
ConditionsYield
In diethylene glycol dimethyl ether Heating;90%
2-Methylthiouracil
5751-20-2

2-Methylthiouracil

4-Chloro-2-methylthiopyrimidine
49844-90-8

4-Chloro-2-methylthiopyrimidine

Conditions
ConditionsYield
With thionyl chloride In dichloromethane; N,N-dimethyl-formamide at 40℃; for 3h;87.6%
With thionyl chloride; N,N-dimethyl-formamide In dichloromethane at 40℃; for 3h;87.6%
With trichlorophosphate
With trichlorophosphate
2-Methylthiouracil
5751-20-2

2-Methylthiouracil

2-methylsulfanyl-5-bromopyrimidin-4-one
81560-03-4

2-methylsulfanyl-5-bromopyrimidin-4-one

Conditions
ConditionsYield
With N-Bromosuccinimide In dichloromethane for 6h; Reflux;87%
With potassium hydroxide; bromine; sodium bromide In 1,4-dioxane at 70℃; for 1h;75%
With bromine; acetic acid at 0 - 20℃; for 16h;62%
2-Methylthiouracil
5751-20-2

2-Methylthiouracil

acrylonitrile
107-13-1

acrylonitrile

3-(2-cyanoethyl)-2-methylthiopyrimidin-4-one
17994-74-0

3-(2-cyanoethyl)-2-methylthiopyrimidin-4-one

Conditions
ConditionsYield
With pyridine for 7h; Heating;86%
2-Methylthiouracil
5751-20-2

2-Methylthiouracil

tributyl(thien-2-yl)stannane
54663-78-4

tributyl(thien-2-yl)stannane

2-thiophen-2-yl-3H-pyrimidin-4-one
125903-92-6

2-thiophen-2-yl-3H-pyrimidin-4-one

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); copper(I) bromide dimethylsulfide complex In tetrahydrofuran for 24h; Liebeskind-Srogl cross-coupling; Inert atmosphere; Reflux;84%
2-Methylthiouracil
5751-20-2

2-Methylthiouracil

3-amino-4-methyl benzoic acid methyl ester
18595-18-1

3-amino-4-methyl benzoic acid methyl ester

methyl 3-(4-oxopyrimidin-2-ylamino)-4-methylbenzoate
1451042-82-2

methyl 3-(4-oxopyrimidin-2-ylamino)-4-methylbenzoate

Conditions
ConditionsYield
With hydrogenchloride In water at 130 - 160℃; for 1.5h; Reagent/catalyst; Temperature; Time; Inert atmosphere;84%
2-Methylthiouracil
5751-20-2

2-Methylthiouracil

4-bromo-2-methylsulfanylpyrimidine
959236-97-6

4-bromo-2-methylsulfanylpyrimidine

Conditions
ConditionsYield
With phosphorus(V) oxybromide In acetonitrile at 80℃; for 5h;83%
2-Methylthiouracil
5751-20-2

2-Methylthiouracil

1,3-dibromo-propane
109-64-8

1,3-dibromo-propane

3-(3-bromopropyl)-S-methyl-2-thiouracil
122182-81-4

3-(3-bromopropyl)-S-methyl-2-thiouracil

Conditions
ConditionsYield
With sodium hydride In N,N-dimethyl-formamide 1h, RT; 60 deg C, 24 h;82%
2-Methylthiouracil
5751-20-2

2-Methylthiouracil

4-chloro-aniline
106-47-8

4-chloro-aniline

2-<(4-chlorophenyl)amino>pyrimidin-4(3H)-one

2-<(4-chlorophenyl)amino>pyrimidin-4(3H)-one

Conditions
ConditionsYield
In diethylene glycol dimethyl ether Heating;79%
With 2-ethoxy-ethanol
With Trimethylacetic acid at 130℃; Inert atmosphere;
2-Methylthiouracil
5751-20-2

2-Methylthiouracil

4-amino-benzoic acid
150-13-0

4-amino-benzoic acid

4-(6-oxo-1,6-dihydro-pyrimidin-2-ylamino)-benzoic acid
919116-69-1

4-(6-oxo-1,6-dihydro-pyrimidin-2-ylamino)-benzoic acid

Conditions
ConditionsYield
In diglyme (diethyleneglycol dimethylether) for 16h; Heating / reflux;79%
In diethylene glycol dimethyl ether for 16h; Heating / reflux;
2-Methylthiouracil
5751-20-2

2-Methylthiouracil

3-chloro-aniline
108-42-9

3-chloro-aniline

2-<(3-chlorophenyl)amino>pyrimidin-4(3H)-one

2-<(3-chlorophenyl)amino>pyrimidin-4(3H)-one

Conditions
ConditionsYield
In diethylene glycol dimethyl ether Heating;77%
In diethylene glycol dimethyl ether for 18h; Heating / reflux;66%
2-Methylthiouracil
5751-20-2

2-Methylthiouracil

3,4-(methylenedioxy)-benzeneboronic acid
94839-07-3

3,4-(methylenedioxy)-benzeneboronic acid

4-(benzo[d][1,3]dioxol-5-yl)-2-(methylsulfanyl)pyrimidine
1388177-38-5

4-(benzo[d][1,3]dioxol-5-yl)-2-(methylsulfanyl)pyrimidine

Conditions
ConditionsYield
Stage #1: 2-Methylthiouracil With triethylamine; bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate In 1,4-dioxane at 20℃; for 2h; Inert atmosphere; Sealed tube;
Stage #2: 3,4-(methylenedioxy)-benzeneboronic acid With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In 1,4-dioxane; water at 100℃; for 4h; Suzuki coupling; Inert atmosphere; Sealed tube; chemoselective reaction;		77%

2-Methylthio-4-pyrimidinol Specification

The 2-Methylthio-4-pyrimidinol, with the CAS registry number 5751-20-2 and EINECS registry number 227-274-6, has the systematic name of 2-(methylsulfanyl)pyrimidin-4(3H)-one. It belongs to the product categoies of Pyrimidine and Intermediate of mizolastine. And the molecular formula of this chemical is C5H6N2OS.

The physical properties of 2-Methylthio-4-pyrimidinol are as followings: (1)ACD/LogP: 0.26; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 0.26; (4)ACD/LogD (pH 7.4): 0.12; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 32.91; (8)ACD/KOC (pH 7.4): 23.75; (9)#H bond acceptors: 3; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 1; (12)Polar Surface Area: 57.97 Å2; (13)Index of Refraction: 1.638; (14)Molar Refractivity: 37.62 cm3; (15)Molar Volume: 104.5 cm3; (16)Polarizability: 14.91×10-24cm3; (17)Surface Tension: 51.1 dyne/cm; (18)Density: 1.35 g/cm3; (19)Flash Point: 136 °C; (20)Enthalpy of Vaporization: 56.3 kJ/mol; (21)Boiling Point: 301.2 °C at 760 mmHg; (22)Vapour Pressure: 0.000597 mmHg at 25°C.

Preparation: This chemical can be prepared by 2-thioxo-2,3-dihydro-1H-pyrimidin-4-one and iodomethane. The reaction will need reagent aq. NaOH, and the yield is about 88%. 

Uses of 2-Methylthio-4-pyrimidinol: It can react with 4-chloro-aniline to produce 2-(4-chloro-anilino)-3H-pyrimidin-4-one. This reaction will need solvent bis-(2-methoxy-ethyl) ether and heating. The yield is about 79%.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C1/C=C\N=C(\SC)N1
(2)InChI: InChI=1/C5H6N2OS/c1-9-5-6-3-2-4(8)7-5/h2-3H,1H3,(H,6,7,8)
(3)InChIKey: UYHSQVMHSFXUOA-UHFFFAOYAO

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