Water → HCID 18948527, compound

Temperature

-37 °C

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%)

1. customof 30 minutes
2. extractionAfter usual work up, the product was extracted with 300 ml of dichloromethane
3. dry with materialThe combined dichloromethane layer was dried over potassium carbonate
4. customthe solvent was evaporated from the filtrate
5. additionTo the resulting oily residue was added 300 ml of hexane
6. temperatureheated to 80° C.
7. stirringwith stirring
8. customAn insoluble oily residue then removed by decantation
9. extractionThe target compound was extracted with 200 ml of hexane from the oily residue
10. customThe combined hexane layer was evaporated

ORD record

ord-6cd83a0d5e7f4a638624c8c50bb9bf7e

Source dataset

uspto-grants-1995_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05378700