Dimethylamine → 5-Dimethylaminomethyl-8-hydroxy-7-propylquinoline

Participants

Reaction Steps

To a cold (0°) solution of 8-hydroxy-7-propylquinoline (5.7 g, 30.4 mmol) and 26% aqueous dimethylamine (15 g, 83 mmol) in 30 mL of ethanol was added dropwise 37% aqueous formaldehyde (4.5 g, 55.4 mmol). After stirring at room temperature for 1 hr, the mixture was refluxed for 2 hr, cooled and evaporated to dryness. The residue was diluted with water, extracted twice with ether and the extracts combined and dried (MgSO4). Evaporation gave 5-dimethylaminomethyl-8-hydroxy-7-propylquinoline as a syrup (7.00 g, 94%), structure confirmed by NMR. A portion of this syrup (2.44 g, 10 mmol) was heated under nitrogen with 2,4-diamino-6-methylthiopyrimidine (1.56 g, 10 mmol) in ethylene glycol (20 mL) at 120°-160° for 1 hr, then cooled. The solid that separated was collected, and washed with ether and hexanes to give the title compound (3.20 g, 90%). An analytical sample was obtained by recrystallization from 95% ethanol, mp. 204°-206° dec. Anal. Calcd for C18H21N5SO: C, 60.82; H, 5.95; N, 19.70; S, 9.02. Found: C, 60.81; H, 5.98; N, 19.67; S, 9.02.

Provenance & Evidence