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588-36-3

588-36-3 Structure

588-36-3 Structure
IdentificationBack Directory
[Name]

(4-AMINO-2-(METHYLTHIO)PYRIMIDIN-5-YL)METHANOL
[CAS]

588-36-3
[Synonyms]

Methioprim
(4-AMINO-2-(METHYLTHIO)PYRIMIDIN-5-YL)ME...
4-AMINO-2-(METHYLTHIO)-5-PYRIMIDINEMETHANOL
(4-AMINO-2-(METHYLTHIO)PYRIMIDIN-5-YL)METHANOL
4-AMINO-2-METHYLMERCAPTO-PYRIMIDINE-4-CARBINOL
4-AMINO-5-HYDROXYMETHYL-2-(METHYLTHIO)PYRIMIDINE
(4-AMINO-2-METHYLSULFANYL-PYRIMIDIN-5-YL)-METHANOL
(4-azanyl-2-methylsulfanyl-pyrimidin-5-yl)methanol
[Molecular Formula]

C6H9N3OS
[MDL Number]

MFCD08236793
[MOL File]

588-36-3.mol
[Molecular Weight]

171.22
Chemical PropertiesBack Directory
[Melting point ]

126-127°
[Boiling point ]

408.6±30.0 °C(Predicted)
[density ]

1.38±0.1 g/cm3(Predicted)
[storage temp. ]

under inert gas (nitrogen or Argon) at 2–8 °C
[solubility ]

DMSO (Slightly), Methanol (Slightly)
[form ]

Solid
[pka]

13.08±0.10(Predicted)
[color ]

Off-White to Pale Yellow
Hazard InformationBack Directory
[Chemical Properties]

White cryst powder
[Uses]

An intermediate used in the synthesis of Thiamine (T344185). Also, used for the preparation of pyridopyrimidines and naphthyridines as inhibitors of Akt kinase for the treatment of cancer.
[Uses]

Tumor antagonist in mice.
[Synthesis]

ETHYL 4-AMINO-2-(METHYLTHIO)PYRIMIDINE-5-CARBOXYLATE

776-53-4

(4-AMINO-2-(METHYLTHIO)PYRIMIDIN-5-YL)METHANOL

588-36-3

General procedure for the synthesis of 2-(methylthio)-4-aminopyrimidine-5-carboxylic acid from ethyl 2-(methylthio)-4-aminopyrimidine-5-carboxylate: ethyl 4-amino-2-(methylthio)pyrimidine-5-carboxylate (72.3 g, 339 mmol) was dissolved in tetrahydrofuran (THF, 900 mL) and the solution was cooled to 0 °C. A solution of LiAlH4 (2 M in THF, 195 mL, 390 mmol) was added slowly and dropwise over 1 hour. The reaction mixture was kept stirred at 0 °C for 2 h, then allowed to warm slowly to room temperature and continued stirring overnight. Upon completion of the reaction, the mixture was again cooled to 0 °C and water (15 mL), 20% aqueous potassium hydroxide solution (15 mL) and water (30 mL) were carefully added in turn to quench the reaction. The resulting mixture was stirred for 1 hour. Subsequently, it was dried with anhydrous magnesium sulfate (MgSO4), filtered, and the filtrate was concentrated under reduced pressure and finally dried under vacuum to afford the target product 2-methylthio-4-aminopyrimidine-5-methanol (55.85 g, 96% yield). Mass spectrometry (MS) analysis showed m/z: 172.1 ([M + H]+).

[References]

[1] Journal of Medicinal Chemistry, 2005, vol. 48, # 7, p. 2371 - 2387
[2] Patent: WO2013/134243, 2013, A1. Location in patent: Page/Page column 16
[3] Journal of Medicinal Chemistry, 2015, vol. 58, # 10, p. 4165 - 4179
[4] Patent: WO2014/151682, 2014, A1. Location in patent: Page/Page column 57; 58
[5] Journal of Medicinal Chemistry, 2014, vol. 57, # 3, p. 578 - 599
Safety DataBack Directory
[Symbol(GHS) ]

Exclamation Mark (GHS07)
GHS07
[Signal word ]

Warning
[Hazard statements ]

H302-H315-H319-H332-H335
[Precautionary statements ]

P280-P305+P351+P338-P310
[HS Code ]

29335990
Raw materials And Preparation ProductsBack Directory
[Raw materials]

Ethanol-->Tetrahydrofuran-->Sodium-->Toluene-->Acetic anhydride-->Lithium Aluminum Hydride-->Isopropyl alcohol-->Triethyl orthoformate-->Ethyl cyanoacetate-->Thiourea-->N,N-Dimethylformamide dimethyl acetal
Spectrum DetailBack Directory
[Spectrum Detail]

(4-AMINO-2-(METHYLTHIO)PYRIMIDIN-5-YL)METHANOL(588-36-3)1HNMR
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