4-Amino-2-(methylthio)pyrimidine-5-carbaldehyde Chemical Properties

Melting point:

183-184 °C

Boiling point:

379.7±27.0 °C(Predicted)

Density 

1.37

storage temp. 

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

pka

2.50±0.10(Predicted)

form 

solid

color 

White

InChI

InChI=1S/C6H7N3OS/c1-11-6-8-2-4(3-10)5(7)9-6/h2-3H,1H3,(H2,7,8,9)

InChIKey

FGONQMFYFJRAIG-UHFFFAOYSA-N

SMILES

C1(SC)=NC=C(C=O)C(N)=N1

Safety Information

HS Code 

2933599590

4-Amino-2-(methylthio)pyrimidine-5-carbaldehyde Usage And Synthesis

Uses

4-Amino-2-(methylthio)pyrimidine-5-carbaldehyde can be used for the preparation of pyridopyrimidines and naphthyridines as inhibitors of Akt kinase for the treatment of cancer.

Synthesis

Method A: Manganese dioxide (MnO2, 49.8 g, 572 mmol) was added to a chloroform (818 mL) suspension of 4-amino-2-(methylthio)pyrimidin-5-ylmethanol (28 g, 164 mmol), and the reaction mixture was stirred for 4 hours at 55°C (internal temperature). After completion of the reaction, the reaction mixture was filtered while hot and the filter cake was washed with hot chloroform and tetrahydrofuran (THF). The filtrates were combined, concentrated under reduced pressure and subsequently dried under vacuum to afford 4-amino-2-methylmercaptopyrimidine-5-carbaldehyde (26.7 g, 96% yield) as a light yellow solid. Mass spectrometry (MS) data: m/z 170.1 ([M+H]+).

References

[1] Journal of Medicinal Chemistry, 2000, vol. 43, # 24, p. 4606 - 4616
[2] Patent: WO2013/134243, 2013, A1. Location in patent: Page/Page column 17
[3] Journal of Medicinal Chemistry, 2015, vol. 58, # 10, p. 4165 - 4179
[4] Patent: WO2014/182829, 2014, A1. Location in patent: Page/Page column 42
[5] Patent: WO2016/191172, 2016, A1. Location in patent: Page/Page column 57

4-Amino-2-(methylthio)pyrimidine-5-carbaldehyde(770-31-0)Related Product Information

• 4-Iodo-2-methylpyridine
• 2-AMINO-3-HYDROXY-4-BROMOPYRIDINE HBR
• 4-CHLORO-6-ETHYLTHIENO[2,3-D]PYRIMIDINE
• 1H-Pyrrolo[2,3-b]pyridine, 4-chloro-6-methyl-
• ETHYL 4-AMINO-2-(METHYLTHIO)PYRIMIDINE-5-CARBOXYLATE
• Ethyl 4-amino-2-(ethylthio)-5-pyrimidinecarboxylate
• 4-AMINO-5-CARBOXY-2-ETHYL-MERCAPTOPYRIMIDINE
• Pyrimidine-5-carboxaldehyde
• {[4-AMINO-5-(ETHOXYCARBONYL)PYRIMIDIN-2-YL]THIO}ACETIC ACID
• ETHYL 4-(4-CHLOROANILINO)-2-(METHYLSULFANYL)-5-PYRIMIDINECARBOXYLATE
• ETHYL 4-(METHYLAMINO)-2-(METHYLSULFANYL)-5-PYRIMIDINECARBOXYLATE
• ETHYL 4-(BENZYLAMINO)-2-(METHYLTHIO)PYRIMIDINE-5-CARBOXYLATE
• 4-AMINO-2-(METHYLTHIO)PYRIMIDINE-5-CARBOXAMIDE
• ETHYL 2-(METHYLSULFANYL)-4-MORPHOLINO-5-PYRIMIDINECARBOXYLATE
• ETHYL 2-(METHYLSULFANYL)-4-PIPERIDINO-5-PYRIMIDINECARBOXYLATE
• ETHYL 4-(3,4-DICHLOROANILINO)-2-(METHYLSULFANYL)-5-PYRIMIDINECARBOXYLATE
• RARECHEM AL FB 0074
• 4-AMINO-2-METHYLSULFANYL-PYRIMIDINE-5-CARBOXYLIC ACID