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

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

Safety Information

HS Code 

29335990

(4-AMINO-2-(METHYLTHIO)PYRIMIDIN-5-YL)METHANOL Usage And Synthesis

Chemical Properties

(4-AMINO-2-(METHYLTHIO)PYRIMIDIN-5-YL)METHANOL is white cryst powder

Uses

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

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

(4-AMINO-2-(METHYLTHIO)PYRIMIDIN-5-YL)METHANOL(588-36-3)Related Product Information

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• ETHYL 4-[3,5-BIS(TRIFLUOROMETHYL)ANILINO]-2-(METHYLSULFANYL)-5-PYRIMIDINECARBOXYLATE
• RARECHEM AL FB 0074
• 4-AMINO-2-METHYLSULFANYL-PYRIMIDINE-5-CARBOXYLIC ACID