Allyl Alcohol → 7-allyl-5-methyl-2-(1-naphthylmethyl)-3-(4-pyridinyl)-2H-pyrazolo[3,4-d]pyrimidine-4,6(5H,7H)-dione

Participants

Reaction Conditions

Reaction Steps

Allyl alcohol (17.7 μL, 0.261 mmol) was dissolved in anh. CH2Cl2 (1 mL) and cooled to −5° C. To this was added methanesulfonyl chloride (20.2 ul, 0.261 mmol) followed by N,N′diisopropylethylamine (45.4 μl, 0.261 mmol). The mixture was stirred at low temperature for 2 h. Meanwhile, 5-methyl-2-(1-naphthylmethyl)-3-(4-pyridinyl)-2H-pyrazolo[3,4-d]pyrimidine-4,6(5H,7H)-dione (100 mg, 0.261 mmol) was suspended in anh. N,N′dimethylacetamide (2 mL) followed by addition of cesium carbonate (85 mg, 0.261 mmol). at room temperature for 1 h. To the mixture was added the preformed mesylate and the mixture was heated at 100 ° C. for 4 h. Reaction was partitioned between ethylacetate and water. The organic phase was washed with water, brine and dried over sodium sulfate and concentrated in vacuo. The crude product was purified by semi prep HPLC eluting with acetonitrile/water/TFA mixtures.

Provenance & Evidence