Ammonium Hydroxide → HCID 14654966, compound

Participants

Reaction Conditions

Reaction Steps

Four mL of 5.25% aqueous sodium hypochlorite (2.8 mmol) was cooled and added to 10 mL of 1.4N ammonium hydroxide. After stirring for 30 min at 0° C., 2-amino-7-(2-deoxy-β-D-erythro-pentofuranosyl) pyrrolo[2,3-d]pyrimidine-4-thione 37 (0.78 g, 2.8 mmol) in 1.3 mL of 2N potassium hydroxide was added and stirred for 1 h at 0° C. The precipitate was collected by filtration, washed with EtOH and dried at 25° C. over P2O5 in vacuo to obtain 670 mg (81%) of the title compound 38. m.p. 162°-164° C. (dec): UV: λmax (pH 1) 238 nm (ε28,500): 347 (5,600): λmax (pH 7) 234 nm (ε35,400), 317 (10,400): λmax (pH 11) 234 nm (ε30,900), 318 (10,300): 1H NMR (DMSO-d6): δ4.11 (s, 2, exchangeable in D2O, SNH2), 6.18 (s, 2, exchangeable in D2O, NH2), 6.44 (dd, 1, J =8.3 and 5.9 Hz, C1'H), 6.61 (d, 1, J =3.8 Hz, C5H), 6.18 (d, 1, J =3.8 Hz, C6H). Anal. Calcd for C11H15N5O3S.1/4H2O: (301.83): C, 43.77: H, 5.17: N, 23.20: S, 10.62. Found: C, 43.59: H, 4.95: N, 23.13: S, 10.32.

Provenance & Evidence