METHYL 5-BROMO-2-(METHYLSULFANYL)-4-PYRIMIDINECARBOXYLATE, 97 Chemical Properties

Melting point:

67 °C

Boiling point:

348.7±22.0 °C(Predicted)

Density 

1.69±0.1 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

pka

-2.91±0.29(Predicted)

form 

Solid

color 

Pale yellow

Water Solubility 

Slightly soluble in water (0.42 g/L).

InChI

InChI=1S/C7H7BrN2O2S/c1-12-6(11)5-4(8)3-9-7(10-5)13-2/h3H,1-2H3

InChIKey

MYZJIEWTRJTWCD-UHFFFAOYSA-N

SMILES

C1(SC)=NC=C(Br)C(C(OC)=O)=N1

Safety Information

Hazard Codes 

Xi

Risk Statements 

43-36/37/38-20/21/22

Safety Statements 

36/37-36/37/39-26-22

RIDADR 

UN2811

HazardClass 

IRRITANT

HazardClass 

6.1

HS Code 

29335990

METHYL 5-BROMO-2-(METHYLSULFANYL)-4-PYRIMIDINECARBOXYLATE, 97 Usage And Synthesis

Chemical Properties

Yellow solid

Uses

It can be used as pharmaceutical raw material and intermediate.

Synthesis

General procedure for the preparation of methyl 5-bromo-2-(methylthio)pyrimidine-4-carboxylate: 5-bromo-2-(methylthio)pyrimidine-4-carboxylic acid (7.64 g, 30.7 mmol) was dissolved in methanol (60 mL). Sulfuric acid (2 mL) was added to the solution and the mixture was subsequently heated to reflux for 24 hours. Upon completion of the reaction, the mixture was poured into ice water and extracted with dichloromethane (DCM). The organic phase was washed with saturated aqueous sodium bicarbonate solution, dried over anhydrous sodium sulfate and concentrated under reduced pressure to afford the target compound methyl 5-bromo-2-(methylthio)pyrimidine-4-carboxylate (6.42 g, 80% yield). The product was characterized by 1H NMR (500 MHz, CDCl3): δ 8.72 (s, 1H), 4.01 (s, 3H), 2.58 (s, 3H).LCMS (ESI) analysis showed a retention time of Rt = 2.35 min and a molecular ion peak 263 [M + H]+.

References

[1] Patent: WO2014/37750, 2014, A1. Location in patent: Paragraph 00149; 0046-0050
[2] Patent: WO2015/128676, 2015, A1. Location in patent: Page/Page column 117-118
[3] Journal of Medicinal Chemistry, 2017, vol. 60, # 6, p. 2215 - 2226
[4] Patent: WO2017/221100, 2017, A1. Location in patent: Paragraph 00284
[5] Patent: EP3305785, 2018, A1. Location in patent: Paragraph 0167; 0168

METHYL 5-BROMO-2-(METHYLSULFANYL)-4-PYRIMIDINECARBOXYLATE, 97(50593-91-4)Related Product Information

• PYRIMIDINE-4-CARBOXYLIC ACID METHYL ESTER
• 5-Bromopyrimidine
• 5-BROMO-4-PYRIMIDINECARBOXALDEHYDE
• 5-Bromo-2-(methylthio)pyrimidine-4-carboxylic acid
• 2-METHYLSULFANYL-PYRIMIDINE-4-CARBALDEHYDE
• 5-BROMO-2-(METHYLTHIO)PYRIMIDINE
• 2-Thiomethylpyrimidine-4-carboxylic acid
• METHYL 5-BROMO-4-PYRIMIDINECARBOXYLATE
• METHYL 5-BROMO-2-(METHYLSULFANYL)-4-PYRIMIDINECARBOXYLATE, 97
• 5-BROMO-4-PYRIMIDINECARBOXYLIC ACID