Ammonia → HCID 15539884, compound

Participants

Reaction Conditions

Reaction Steps

A soln. of compd. 6-amino-1-[2-deoxy-β-D-erythro-pentofuranosyl]-3-iodo-4-isopropoxy-1H-pyrazolo[3,4-d]pyrimidine 12 (F. Seela, G. Becher, Synthesis 1998, 2, 207.) (1 g, 2.3 mmol) in a aq. 25% NH3 soln. (80 ml) was heated at 70° C. for 4 d. The solvent was evaporated to dryness, the residue dissolved in hot water and crystallized. Colorless needles (640 mg, 71%). M.p. 154°. TLC (A): Rf0.2. UV (MeOH): 223 (31800), 260 (8700), 278 (9100). 1H-NMR ((D6)DMSO): 2.12 (m, Hα—C(2′)); 2.67 (m, Hβ—C(2′)); 3.38, 3.44 (m , H2—C(5′)); 3.73 (m , H—C(4′)); 4.33 (m, H—C(3′)); 4.73 (t, J=5.7, OH—C(5′)); 5.17 (d, J=4.3, OH—C(3′)); 6.27 (‘t’, J=6.5, H—C(1′)); 6.34 (br, NH2); 6.62 (br, NH2). Anal. calc. for C10H13IN6O3 (392.2): C, 30.63; H, 3.34; N, 21.43; Found: C, 30.91; H 3.61; N, 21.27.

Provenance & Evidence