m-Chloroperbenzoic acid → HCID 14654976, compound

Participants

Reaction Conditions

Reaction Steps

2-Amino-7-(2-deoxy-β-D-erythro-pentofuranosyl)pyrrolo[2,3-d1pyrimidine-4-sulfenamide 38 (300 mg, 1 mmol) was suspended in EtOH (120 mL) and cooled to 0° C. m-Chloroperoxybenzoic acid (85%, 100 mg, 1 mmol) in EtOH (30 mL) was added dropwise during 1.5 h. After stirring for an additional 30 min at 0° C., the mixture was concentrated to 10 mL in vacuo below 25° C. Ethyl ether (100 mL) was added to the concentrate solution and allowed to stand in the refrigerator overnight. The precipitate was collected by filtration, washed with ethyl ether and dried at 25° C. under reduced pressure to yield 110 mg (35%) of desired compound 39: m.p. 122 C (dec): UV: λmax (pH 1) 352 nm (ε3,100): 272 (3,100), 240 (21,100): λmax (pH 7 ) 336 nm (ε4,800), 239 (21,500): λmax (pH 11) 337 nm (ε4,600), 239 (20,500): IR (KBr) 1060 (S=O) cm-1 :1H NMR (DMSO-d6): δ6.45 (s, 2, exchangeable in D2O, SONH2), 6.49, (dd, 1, J =8.3 and 5.9 Hz, C1'H), 6.62 (s, 2, exchangeable in D2O, NH2), 6.73 (d, 1, J 3.8 Hz, C5H), 7.38 (d, 1, J =3.8 Hz, C6H). Anal. Calcd for C11H15N5O4S: C, 42.16: H, 4.82: N, 22.35: S, 10.23. Found: C, 41.91: H, 4.86: N, 22.07: S, 9.91.

Provenance & Evidence