Water → HCID 18948527, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 69 g (370 nmol) of 2-amino-4-chloro-5,6,7,8-tetrahydropyrido[2,3-d]pyrimidine in anhydrous dichloromethan (450 ml) was added 70 ml (500 mmol) of triethylamine, and then cooled to -37° C. Then, under inert gas atmosphere, to the reaction mixture was dropwise added 102 ml (450 mmol) of tertbutyldimethylsilyl trifluoromethanesulfonate over a period of 30 minutes, and the mixture was stirred at that temperature for 1.5 hours. The suspension turned to a red-colored solution. The reaction solution was poured into 300 ml of water. After usual work up, the product was extracted with 300 ml of dichloromethane. The combined dichloromethane layer was dried over potassium carbonate, and then the solvent was evaporated from the filtrate. To the resulting oily residue was added 300 ml of hexane, then heated to 80° C. with stirring. An insoluble oily residue then removed by decantation. The target compound was extracted with 200 ml of hexane from the oily residue. The combined hexane layer was evaporated to give 112 g (370 mmol) of 2-tert-butyldimethylsilylamino-4-chloro-5,6,7,8tetrahydropyrido[2,3-d]pyrimidine in the form of white crystals. (Yield 99%)

Provenance & Evidence