2-METHYLSULFANYL-PYRIMIDINE-4-CARBALDEHYDE Chemical Properties

Melting point:

68°C

Boiling point:

110-112 °C(Press: 0.001 Torr)

Density 

1.29±0.1 g/cm3(Predicted)

storage temp. 

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

pka

-0.87±0.23(Predicted)

form 

solid

color 

Off-white

Safety Information

Safety Statements 

24/25

HS Code 

2933599590

2-METHYLSULFANYL-PYRIMIDINE-4-CARBALDEHYDE Usage And Synthesis

Uses

4-Formyl-2-methylthiopyrimidine is used in the synthesis of cytokine synthesis inhibitors.

Synthesis

Example 4 Synthesis of 2-(methylthio)pyrimidine-4-carboxaldehyde (4): 4-(dimethoxymethyl)-2-(methylthio)pyrimidine (3) (53.7 g, 268 mmol) was slowly added to an aqueous solution of 1.2N HCl (300 mL, 268 mmol, 1.0 eq.) at 60 °C with continuous stirring for 3 hours. Upon completion of the reaction, the mixture was cooled to room temperature and neutralized by slow addition of solid sodium bicarbonate. Subsequently, the crude product was extracted with ether (3 x 150 mL) and the combined organic layers were concentrated under reduced pressure to afford the target product 2-(methylthio)pyrimidine-4-carboxaldehyde (4) as a yellow solid (14.2 g, 34% yield).LC-MS m/z 155 (M+1). Reference: WO 2006/009734 A1, p. 67.

References

[1] Journal of Medicinal Chemistry, 2015, vol. 58, # 3, p. 1067 - 1088
[2] Patent: WO2016/7966, 2016, A2. Location in patent: Paragraph 0024
[3] Journal of Medicinal Chemistry, 2018,
[4] Patent: US2011/152235, 2011, A1. Location in patent: Page/Page column 67
[5] Patent: WO2011/103289, 2011, A2. Location in patent: Page/Page column 73; 74

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