Water → 3-amino-6-(1-phenylcyclopropyl)pyridine-2(1H)-thione

Reaction equation

CC1[S:3][C:4]2[C:9]([N:10]=1)=[CH:8][CH:7]=[C:6]([C:11]1([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH2:13][CH2:12]1)[N:5]=2.[OH-].[Na+].O>CCO>[NH2:10][C:9]1[C:4](=[S:3])[NH:5][C:6]([C:11]2([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH2:13][CH2:12]2)=[CH:7][CH:8]=1

Participants

Procedure

A slurry of 2-methyl-5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridine (17.0 g, 63.8 mmol) in 128 mL EtOH was added sodium hydroxide 10 M in water (128 mL, 1276 mmol). Argon was bubbled through the resulting slurry for 5 min, then the reaction flask was fitted with a water-cooled reflux condenser, flushed with argon, and the reaction mixture was heated to vigorous reflux under argon. After 6 h, the reaction mixture was cooled and the EtOH was removed in vacuo. The resulting slurry was poured onto ice and neutralized with 260 mL 5N aq. HCl to pH 4. A light yellow precipitate resulted. The solid was collected by filtration through a glass frit, rinsing with 2×200 mL water, and the solid was dried under a bag of nitrogen overnight. Further drying in vacuo for several hours gave 3-amino-6-(1-phenylcyclopropyl)pyridine-2(1H)-thione as a light yellow solid. MS (ESI) m/z: calculated: 242.1; Observed: 243.1 (M++1).