2-Chloropyrimidine-5-carboxylic acid → HCID 53235488, compound

Participants

Reaction Conditions

Reaction Steps

2-Chloro-pyrimidine-5-carboxylic acid (23 mg) was dissolved in methanol (1 ml) and the solution cooled to 0° C. before addition of 4-(4,6-dimethoxy[1.3.5]triazin-2-yl)-4-methylmorpholinium chloride hydrate (45 mg). The reaction mixture was stirred for 5 minutes at 0° C. before dropwise addition of a solution of (S)-4-[2-(4-Amino-phenyl)-ethyl]-4,5-dihydro-oxazol-2-ylamine (30 mg) in methanol (1 ml). Stirring at 0° C. was continued for 1 hour before quenching by addition of a 1N solution of sodium hydroxide. The reaction mixture was then extracted three times with ethyl acetate and the combined organic layers washed with brine, dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by preparative HPLC to give 2-methoxy-pyrimidine-5-carboxylic acid {4-[2-((S)-2-amino-4,5-dihydro-oxazol-4-yl)-ethyl]-phenyl}-amide (9 mg) as a yellow solid. MS (ISP): 342.2 ([M+H]+).

Provenance & Evidence