Tetrahydrofuran → HCID 136009431, compound

Participants

Reaction Steps

To a solution of ethyl 2-((1R,3R,4S)-3-ethyl-4-(6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazin-1-yl)cyclopentyl)acetate (0.166 g, 0.486 mmol, Example #38, Step H) in THF (4 mL) at about 0° C. was added lithium chloride in THF (0.5 M, 3.9 mL) followed by methylmagnesium bromide in Et2O (3.0 M, 0.65 mL). After about 20 min the reaction mixture was allowed to warm to rt. After about 4 h the reaction mixture was cooled to about −78° C. and saturated aqueous NH4Cl (about 5 mL) was added. After about 5 min the reaction mixture was allowed to warm to rt and EtOAc (about 10 mL) was added. The layers were separated and the organic solution was dried over anhydrous MgSO4, filtered, and concentrated under reduced pressure. The crude material was purified by silica gel chromatography eluting with EtOAc/MeOH to provide 1-((1R,3R,4S)-3-ethyl-4-(6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazin-1-yl)cyclopentyl)-2-methylpropan-2-ol (0.118 g, 74%) as a foam: LC/MS (Table 1, Method a) Rt=1.64 min; MS m/z 328 (M+H)+.

Provenance & Evidence