Hydroxylamine → (S)-2-(6-(5-Methylpyridin-2-yl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-ylamino)-2-(4-(trifluoromethyl)phenyl)ethanol

Participants

Reaction Steps

A reaction mixture of 4-chloro-5,6,7,8-tetrahydro-6-(5-methylpyridin-2-yl)pyrido[4,3-d]pyrimidine (150 mg, 0.58 mmol) and (S)-2-amino-2-(4-(trifluoromethyl)phenyl)ethanol (180 mg, 0.86 mmol) in acetonitrile (3 mL) and N,N-diisopropylethylamine (0.20 mL, 1.2 mmol) was run in a microwave reactor at 180° C. for 2 h. LC-MS indicated amino alcohol was consumed and about 50% conversion of the chloride. Additional (S)-2-amino-2-(4-(trifluoromethyl)phenyl)ethanol (100 mg) was added and the mixture was run microwave reaction at 160° C. for another 2 h. The reaction mixture was treated with aq. Na2CO3 and EtOAc (150 mL). The organic layer was separated and washed with brine, dried (Na2SO4), and concentrated. The residue was purified by semi-prep HPLC to give a white powder.

Provenance & Evidence