Benzyl Alcohol → HCID 67538861, compound

Participants

Reaction Conditions

Reaction Steps

A sealed tube charged with 4-(5-Iodo-pyrimidin-4-yl)-piperazine-1-carboxylic acid tert-butyl ester (780 mg, 2.00 mmol), CuI (38 mg, 0.20 mmol), 1,10-phenathroline (72 mg, 0.4 mmol), Cs2CO3 (912 mg, 2.8 mmol), benzyl alcohol (0.62 mL, 6.0 mmol) and toluene (2 mL) was heated at 110° C. for 40 hours. The resulting suspension was cooled to room temperature and filtered through a silica gel pad, eluting with EtOAc. Evaporation of the solvent followed by flash chromatography on silica gel (10:1 hexanes/EtOAc) provided 4-(5-benzyloxypyrimidin-4-yl)-piperazine-1-carboxylic acid tert-butyl ester (0.640 g, 86%) as a white solid. 1H NMR (CDCl3, 400 MHz) δ 8.36 (s, 1H), 7.99 (s, 1H), 7.39 (m, 5H), 5.08 (s, 2H), 3.73 (m, 4H), 3.48 (m, 4H), 1.47 (s, 9H). LCMS (APCI+) m/z 371 [M+H]+; Rt=2.52 minutes.

Provenance & Evidence