Ammonia → HCID 15539884, compound

HRID 1293515Notes

Reaction equation

[NH2:1][C:2]1[N:7]=[C:6]2[N:8]([C@@H:12]3[O:17][C@H:16]([CH2:18][OH:19])[C@@H:14]([OH:15])[CH2:13]3)[N:9]=[C:10]([I:11])[C:5]2=[C:4](OC(C)C)[N:3]=1.[NH3:24]>>[C@@H:12]1([N:8]2[C:6]3=[N:7][C:2]([NH2:1])=[N:3][C:4]([NH2:24])=[C:5]3[C:10]([I:11])=[N:9]2)[O:17][C@H:16]([CH2:18][OH:19])[C@@H:14]([OH:15])[CH2:13]1

Participants

Reactant 2

HCID 222Ammonia

HCID 15539883HCID 15539883, compound

Product 1

HCID 15539884HCID 15539884, compound

Conditions

Temperature: 70 °C

Procedure

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.

Workup

customThe solvent was evaporated to dryness
dissolutionthe residue dissolved in hot water
customcrystallized

Sources & evidence

ORD record: ord-a55e98ff3a3741598cc55161410c9a3c
Source dataset: uspto-grants-2007_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07238795B2

Reaction notes

Loading…