5-Bromo-2-(methylthio)pyrimidine-4-carboxylic acid Chemical Properties

Melting point:

158-162 °C (dec.)

Boiling point:

414.5±30.0 °C(Predicted)

Density 

1.91±0.1 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

form 

solid

pka

1.31±0.10(Predicted)

Appearance

Light yellow to brown Solid

InChI

InChI=1S/C6H5BrN2O2S/c1-12-6-8-2-3(7)4(9-6)5(10)11/h2H,1H3,(H,10,11)

InChIKey

YJEWVVYJOJJLBP-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

50593-92-5(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38-20/21/22

Safety Statements 

26-36/37-28

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29335990

MSDS

• Language:English Provider:SigmaAldrich

5-Bromo-2-(methylthio)pyrimidine-4-carboxylic acid Usage And Synthesis

Chemical Properties

White to yellow to light brown solid

Synthesis

Mucobromic acid (58.05 g, 0.225 mol) was slowly added to a stirring aqueous solution (500 mL) of S-methylisothiourea sulfate (62.66 g, 0.225 mol) at room temperature. Subsequently, the reaction suspension was cooled to 10 °C (using an ice bath) and triethylamine (94.1 mL, 0.675 mol) was added dropwise over 4 hours. After the dropwise addition was completed, the reaction mixture was allowed to stand at room temperature for 24 hours. Upon completion of the reaction, activated carbon (Darco G-60) was added to the dark red/brown solution and the activated carbon was removed by filtration after stirring for 10 minutes. The filtrate was acidified with concentrated hydrochloric acid (50 mL) and the precipitated yellow precipitate was collected by filtration and washed sequentially with water (2 x 80 mL) and ether (2 x 100 mL). Finally, the product was dried in a vacuum oven at 50 °C for 2 days to afford 2-(methylthio)-5-bromo-4-pyrimidinecarboxylic acid (33.13 g, 59% yield) as a yellow amorphous solid.1H NMR (DMSO-d6, 400 MHz) δ: 2.75 (s, 3H), 9.20 (s, 1H).

References

[1] Collection of Czechoslovak Chemical Communications, 1980, vol. 45, # 2, p. 539 - 547
[2] Patent: WO2006/66172, 2006, A1. Location in patent: Page/Page column 50
[3] Patent: WO2017/221100, 2017, A1. Location in patent: Paragraph 00283
[4] Patent: WO2014/99836, 2014, A1. Location in patent: Page/Page column 29; 30

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