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

Melting point:

127-128 °C

Boiling point:

370.3±22.0 °C(Predicted)

Density 

1.31±0.1 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

form 

solid

pka

2.46±0.10(Predicted)

Appearance

White to off-white Solid

InChI

InChI=1S/C8H11N3O2S/c1-3-13-7(12)5-4-10-8(14-2)11-6(5)9/h4H,3H2,1-2H3,(H2,9,10,11)

InChIKey

QINRQIZOBCQKAZ-UHFFFAOYSA-N

SMILES

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

Safety Information

Hazard Codes 

Xi

Risk Statements 

43

Safety Statements 

36/37-24/25

HS Code 

29335990

ETHYL 4-AMINO-2-(METHYLTHIO)PYRIMIDINE-5-CARBOXYLATE Usage And Synthesis

Chemical Properties

White solid

Uses

Ethyl 4-amino-2-(methylthio)pyrimidine-5-carboxylate is used for preparation of pyrimidopyrimidines as protein kinase inhibitors.

Synthesis

Step 1. Ethyl 4-chloro-2-(methylthio)pyrimidine-5-carboxylate (100 g, 0.43 mol), tetrahydrofuran (THF, 500 mL) and triethylamine (TEA, 186 mL, 1.29 mol) were added sequentially to a 2L three-neck flask. 28% aqueous ammonium hydroxide solution (400mL) was added in batches under stirring and the reaction temperature was controlled to be below 30°C. After 2 hrs of reaction, water (1000 mL) was added and THF was removed by vacuum distillation.The reaction mixture was filtered and the solid product was collected and dried under vacuum at 50 °C to afford ethyl 4-amino-2-(methylthio)pyrimidine-5-carboxylate as a white solid (90 g, 99% yield). The product was analyzed by LC/MS showing m/z = 213.9 [M+H]+; 1H-NMR (DMSO-d6, 400MHz) δ 8.57 (s, 1H), 8.03 (br, 1H), 7.65 (br, 1H), 4.27 (q, J = 7.5Hz, 2H), 2.46 (s, 3H), 1.29 (t, J = 7.2Hz , 3H).

References

[1] Patent: US2015/31674, 2015, A1. Location in patent: Paragraph 0319
[2] ACS Medicinal Chemistry Letters, 2015, vol. 6, # 12, p. 1241 - 1246
[3] Journal of Medicinal Chemistry, 2016, vol. 59, # 11, p. 5520 - 5541
[4] Patent: WO2014/182829, 2014, A1. Location in patent: Page/Page column 42
[5] Patent: WO2015/120049, 2015, A1. Location in patent: Page/Page column 126; 127

ETHYL 4-AMINO-2-(METHYLTHIO)PYRIMIDINE-5-CARBOXYLATE(776-53-4)Related Product Information

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