2-Methoxyethanol → 5-tert-butyl-2-[4-(2-methoxyethoxy)phenyl]2H-pyrazol-3-ylamine

Participants

Reaction Steps

A mixture of 4-(5-amino-3-tert-butyl-pyrazol-1-yl)phenol (500 mg, 2.16 mmol), 2-methoxyethanol (164.5 mg, 2.16 mmol), ADDP (818.2 mg, 3.24 mmol, 1.5 eq), and triphenylphosphine (850.5 mg, 3.24 mmol, 1.5 eq) in anhydrous THF was stirred at ambient temperature under nitrogen for 18 h. The reaction mixture was poured into EtOAc, and the organic layer was washed with water and brine, dried over Na2SO4, filtered, and concentrated at reduced pressure. Purification by MPLC (eluting with 25% EtOAc/hexane) gave an oil which solidified upon standing, 507 mg (81%). 1H-NMR (DMSO-d6) δ 7.39 (dd, J=6.6, 2.4 Hz, 2H), 6.97 (dd, J=6.9, 2.7 Hz, 2H), 5.30 (s, 1H), 5.02 (broad s, 2H), 4.09 to 4.06 (m, 2H), 3.65 to 3.62 (m, 2H), 3.28 (s, 3H), 1.16 (s, 9H); MS LC-MS [M+H]+=290, RT=1.35 min.

Provenance & Evidence