2-Chlorobenzaldehyde → HCID 67447519, compound

Participants

Reaction Steps

Dissolve 6-chloro-2-methyl-N4-(2-(methylthio)ethyl)pyrimidine-4,5-diamine (28.1 g, 120.7 mmol), and N-methyl piperazine (14.76 ml, 132.81 mmol) in methoxybenzene in a 2 L round bottom flask. Add 2-chlorobenzaldehyde (20.38 mL, 181.1 mmol) in one portion and raise the temperature to 140° C. and maintain at this temperature for 4 days. Cool the reaction mixture and concentrate under reduced pressure. Dilute the resulting oil with 2 N aqueous hydrogen chloride (200 mL) and wash with dichloromethane (500 mL). Discard the organic layer. Treat the aqueous layer with a sodium hydroxide solution until pH=14 is attained. Extract into dichloromethane. Dry the organics over anhydrous sodium sulfate, filter, and concentrate to give the title compound as a brown oil (43 g). ES/MS m/z 417 (M+1).

Provenance & Evidence