Triethylamine → HCID 44216363, compound

Participants

Reaction Steps

To a mixture of 3-amino-6-(1-isopropyl-6-oxo-1,6-dihydro-3-pyridyl)-5-phenyl-2-pyrazinecarboxylic acid (70 mg) and NEt3 (40.4 mg) in THF (0.7 ml), was added isobutyl chloroformate (32.7 mg) under ice-bath cooling. After 1.5 hours stirring at the same temperature, the mixture was poured into a mixture of sodium borohydride (30.2 mg) in a mixture of THF (0.7 ml) and water (1.4 ml) under ice-bath cooling. After 2.5 hours stirring at the same temperature, the mixture was diluted with water and EtOAc, and then the organic layer was separated, washed with water and brine, and dried over MgSO4. The solvent was removed under reduced pressure. The residue was purified by silica-gel column chromatography (CH2:Cl2:MeOH=25:1-10:1). A desired fraction was triturated with IPE to give 5-[5-amino-6-(hydroxymethyl)-3-phenyl-2-pyrazinyl]-1-isopropyl-2(1H)-pyridone (24 mg).

Provenance & Evidence