反应详情

9-(trans-4-Methoxycyclohexyl)-2-(3-hydroxyphenyl)-8-oxo-8,9-dihydro-7H-purine-6-carboxamide. Methyl 9-(trans-4-methoxycyclohexyl)-8-oxo-2-(3-(triisopropylsilyloxy)phenyl)-8,9-dihydro-7H-purine-6-carboxylate (0.205 g, 370 mmol) was dissolved in methanol (15 mL) reacted with ammonia gas according to General Procedure G. After 16 h, the solution was condensed under reduced pressure and the resultant crude product diluted with tetrahydrofuran (15 mL) and 1.0M tetrabutylammonium fluoride in tetrahydrofuran (0.92 mL) was added. After two h, the resulting precipitate was filtered and washed with tetrahydrofuran followed by hexanes. The product was purified using reverse-phase preparative HPLC (20 to 100% acetonitrile+0.1% TFA in H2O+0.1% TFA, over 30 min) to afford the title compound (0.093 g, 66%). 1H NMR (400 MHz, DMSO-d6) δ 11.51 (s, 1H), 9.55 (s, 1H), 8.33 (s, 1H), 8.01 (d, J=7.59, 1H), 7.91 (s, 1H), 7.89 (s, 1H), 7.29 (t, J=7.99, 1H), 6.7 (dd, J=7.59, 1.59, 1H), 4.27 (m, 1H), 3.34 (s, 3H), 3.31 (s, 1H), 2.18 (d, J=10.79, 2H), 1.82 (d, J=11.19, 2H), 1.31 (q, J=12.39, 2H); MS (ESI) m/z 384.4 [M+1]+; mp 355-357° C.

1. customcondensed under reduced pressure
2. additionwas added
3. filtrationAfter two h, the resulting precipitate was filtered
4. washwashed with tetrahydrofuran
5. customThe product was purified
6. customreverse-phase preparative HPLC (20 to 100% acetonitrile+0.1% TFA in H2O+0.1% TFA, over 30 min)