2-METHYLTHIO-4-BROMOPYRIMIDINE synthesis

Yield:959236-97-6 83%

Reaction Conditions:

with phosphorus(V) oxybromide in acetonitrile at 80; for 5 h;

Steps:

695.1 4-bromo-2-(methylthio)pyrimidine
To a stirred solution of 2-(methylthio)pyrimidin-4(3H)-one (5 g, 35.21 mmol, leq) in ACN (lOOmL) was added POBr₃ (12.1 g, 42.3 mmol, 1.2 eq) at RT, then the reaction mixture was heated to 80°C for 5h. Monitored by TLC, the reaction mixture was cooled to RT and quenched in ice cold water then extracted with EtOAc (2X100mL). The combined organic layer was dried over Na₂SC>4 and concentrated to crude compound. The crude compound was purified by column chromatography (silica gel, 100-200 mesh) using 0-10% EtOAc in pet ether as eluent to afford 4- bromo-2-(methylthio)pyrimidine (6g, 83%) as off-white solid. LCMS: [M+H]+ 204.9.

References:

ONTARIO INSTITUTE FOR CANCER RESEARCH (OICR);AL-AWAR, Rima;ZEPEDA-VELAZQUEZ, Carlos Armando;PODA, Gennady;ISAAC, Methvin;UEHLING, David;WILSON, Brian;JOSEPH, Babu;LIU, Yong;SUBRAMANIAN, Pandiaraju;MAMAI, Ahmed;PRAKESCH, Michael;STILLE, Julia Kathleen WO2017/147700, 2017, A1 Location in patent:Paragraph 001094

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