3-[(2S)-oxiran-2-yl]pyridine → HCID 178526826, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of N4-[(trans-4-aminocyclohexyl)methyl]-5-nitro-N2-[2-(trifluoromethoxy)benzyl]pyrimidine-2,4-diamine (124 mg, 0.28 mmol), (S)-3-oxiranyl-pyridine (34 mg, 0.28 mmol) and lithium perchlorate (60 mg, 0.56 mmol) in CH3CN was heated to 100° C. in a sealed tube and stirred for 1 h. The reaction mixture was concentrated and diluted with ethyl acetate. The solution was then treated with 1M Na2CO3 and the organic phase was separated. The aqueous phase was re-extracted with ethyl acetate (×2). The combined organic phase was dried over Na2SO4 and concentrated. The resulting residue was purified by silica gel prep TLC using 10:1:0.05 CH2Cl2:MeOH:NH4OH as an eluent to afford 15 mg of the title compound as an off-white solid (10%), m/z 562.7 [M+1]+.

Provenance & Evidence