Triethylamine → Tert-butyl 5-(2,4-dichlorophenyl)-2-(hydroxymethyl)-7-methylimidazo[1,2-a]pyrimidine-6-carboxylate

Participants

Reaction Steps

To a stirred solution of 6-(tert-butoxycarbonyl)-5-(2,4-dichlorophenyl)-7-methylimidazo[1,2-a]pyrimidine-2-carboxylic acid (400 mg, 0.95 mmol) in THF (6 mL) at room temperature was added ClCOOEt (0.14 mL, 1.42 mmol) and Et3N (0.26 mL, 1.9 mmol). After 1.5 h, the reaction was filtered to remove the insolubles and to the filtrate at 0° C. was added NaBH4 (72 mg, 1.9 mmol) in H2O (0.2 mL). After 30 min, the reaction was quenched with 1N HCl and diluted with EtOAc. The organic layer was washed with satd aq NH4Cl and brine prior to drying over MgSO4. Filtration and concentration under reduced pressure afforded the crude tert-butyl 5-(2,4-dichlorophenyl)-2-(hydroxymethyl)-7-methylimidazo[1,2-a]pyrimidine-6-carboxylate (400 mg, 100% crude yield) which was moved on to next step without further purification.

Provenance & Evidence