Hydrochloric Acid → HCID 18763650, compound

Participants

Reaction Steps

To a suspension of 480 mg (1.57 mmol) of (E)-4-methyl-2-[2-(3-nitro-phenyl)-vinyl]-6-pyrrolidin-1-yl-pyrimidine in 12 ml ethanol were added at RT 1.41 g (6.28 mmol) stannous chloride dihydrate followed by dropwise addition of 1 ml 36% HCl. The mixture was stirred at RT for 12 h, the pH adjusted to pH 7 by dropwise addition of 3N NaOH and then extracted several times with AcOEt. The organic layers were combined, dried over Na2SO4 and concentrated in vacuo. The residue was applied to a silica gel column with CH2Cl2/MeOH (10/1) as eluent. Combination of the purified fractions and evacuation in vacuo gave 289 mg (65.7%) of the desired (E)-3-[2-(4-methyl-6-pyrrolidin-1-yl-pyrimidin-2-yl)-vinyl]-phenylamine as a yellow solid. ISP mass spectrum, m/e: 281.2 (M+1 calculated for C17H20N4: 281).

Provenance & Evidence