Ammonia → 3-(6-Amino-9H-purin-9-yl)cyclopentane-1,2-diol

HRID 2248360Notes

Reaction equation

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

Participants

Reactant 2

HCID 222Ammonia

HCID 57172738HCID 57172738, compound

Product 1

HCID 736513-(6-Amino-9H-purin-9-yl)cyclopentane-1,2-diol

Procedure

(±)-(1R*,2S*,3R*)-3-(6-Chloro-9H-purin-9-yl)-1,2-cyclopentanediol (4.00 g, 15.7 mmol) and ammonia (1, 100 ml) were stirred in a Parr bomb at 25° C. for 18 hours. Evaporation and neutralization with 1N NaOH (16 ml), followed by elution of a silica gel column with MeOH:CHCl3 /1:4 gave title compound as white crystals, recrystallized from 95% ethanol (3.54 g, 96%); mp 201°-202° C.; 1H-NMR (Me2SO-d6) δ8.19 and 8.12 (both s, 2, purine H-2, H-8), 7.18 (br s, 2, NH2), 4.98 (d, J=6.6, 1, 2-OH), 4.76-4.64 (m) overlapping 4.70 (d, J=3.4, 2, H-3 and 1-OH), 4.42-4.34 (m, 1, H-2), 4.04-3.97 (m, 1, H-1), 2.5-1.9 and 1.7-1.6 (both m, 4, two CH2).

Workup

customEvaporation and neutralization with 1N NaOH (16 ml)
washfollowed by elution of a silica gel column with MeOH

Sources & evidence

ORD record: ord-96cb32ba7d8443de9b9afb70459e7b2e
Source dataset: uspto-grants-1991_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05039689

Reaction notes

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