Boron tribromide → HCID 136360264, compound

Participants

Reaction Steps

To a solution of 3,6-diethyl-5-(2,4-dimethoxyphenyl)-[N-(1-ethylpropyl)]pyrazine-2-amine (910 mg, 2.54 mmol) (obtained in example 23) in dichloromethane was added BBr3 (1N,6 ml)at −78° C. The mixture is stirred for 10 min then gradually warmed to room temperature and stirred for 3 hr before being poured into ice-water and extracted with dichloromethane. The aqueous layer was basified with sat. NaHCO3 and extracted with dichloromethane. The combined extracts were dried (sodium sulfate), filtered, concentrated and the residue is purified by column (20% EtOAc in hexane) to give 3,6-diethyl-5-(2,4-dihydroxyphenyl)-[N-(1-ethylpropyl)]pyrazine-2-amine as a yellow oil(590 mg, 71%): 1H NMR (CDCl3, 400 MHz) δ 0.94 (t, 6H), 1.30 (t, 3H), 1.36 (t, 3H), 1.57 (m, 2H), 1.67 (m, 2H), 2.62 (q, 2H), 2.86 (q, 2H), 4.15 (m, 2H). 6.41 (t, 1H), 6.51 (d, 1H), 7.27 (d, 1H). LC-MS: 330 (M+1).

Provenance & Evidence