Acetic Acid → HCID 178437174, compound

Participants

Reaction Steps

To a mixture of 5.0 g (15.1 mmol) of N-[4-hydroxy-5-(trimethylsilyl) ethynyl-7H-pyrrolo[2,3-d]pyrimidin-2-yl]-2,2-dimethylpropionamide, in 40 mL of DMF and 10 mL of tetrahydrofuran was added 6.6 g (15.1 mmol) of tetrabutylammonium fluoride hydrate and the resulting solution was stirred at ambient temperature for 3.5 hours. After addition of 1.18 g of acetic acid and stirring for 15 minutes the mixture was poured into 50 mL of water. After stirring for about 1 hour the resulting suspension was filtered and the precipitate washed with water and dried, affording 3.38 g (86%) of N-(4-hydroxy-5-ethynyl-7H-pyrrolo[2,3-d]pyrimidin-2-yl)-2,2-dimethylpropionamide, mp>300° C. NMR δ1.21 (s, 9H) , 3.89 (s, 1H), 7.28 (s, 1H), 10.82 (br s, 1H), 11.82 (br s, 1H), 11.85 (br s, 1 H); IR (KBr) 3354, 3250, 2973, 2120, 1699, 1676, 1608, 1536, 1433, 1243 cm-1 ; UV (EtOH) 292 nm (ε13,900), 280 nm (ε14,500), 236 nm (ε14,900). Anal. Calcd for C13H14N4O2 : C, 60.46; H, 5.46; N, 21.69. Found: C, 60.25; H, 5.32; N, 21.49.

Provenance & Evidence