Water → HCID 86665993, compound

Participants

Reaction Steps

Then, 44.0 g (115.6mmol) of tert-butyldimethylsilylamino-4-chloro-7H-pyrrolo[2,3-d]pyrimidine and 13.5 ml (1.4 eq.) of methyl iodide in 150 ml of DMF, and 34.40 g (1.6 eq.) of potassium carbonate was reacted at room temperature for 15 hours with vigorous stirring. After addition of water to the reaction mixture, the aqueous solution was extracted with hexane (200 ml×4), washed with brine, and dried over anhydrous magnesium sulfate. The solvents were removed in vacuo, to give 45.87 g (154.5 mmol) (quantitative yield) of 2-ter-butyl-dimethylsilylamino-4-chloro-7-methyl-7H-pyrrolo[2,3-d]pyrimidine in the form of light yellow crystals. Under nitrogen atmosphere the crystals and 21.19 ml (1.5 eq.) of allyl iodide were dissolved in 300 ml of DMF, and the reaction mixture was cooled to 0° C. with vigorous stirring, then 9.27 g (1.5 eq.) of sodium hydride (60%), thoroughly washed by hexane, was added to that as hexane suspension.

Provenance & Evidence