Ammonia → [(1R,4S)-4-(6-aminopurin-9-yl)cyclopent-2-en-1-yl]methanol

HRID 1241358Notes

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][C@@H:14]([CH2:16][OH:17])[CH:13]=[CH:12]1.[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][C@@H:14]([CH2:16][OH:17])[CH:13]=[CH:12]1

Participants

Reactant 2

HCID 222Ammonia

HCID 11994303(1R,cis)-4-(6-Chloro-9H-purin-9-yl)-2-cyclopentene-1-methanol

Product 1

HCID 466400[(1R,4S)-4-(6-aminopurin-9-yl)cyclopent-2-en-1-yl]methanolYield 87%

Procedure

(1R,cis)-4-(6-Chloro-9H-purin-9-yl)-2-cyclopentene-1-methanol (from part e of this example, 2.00 g, 7.98 mmol) was stirred in liquid ammonia (50 mL) in a Parr bomb at 25° C. for 18 hours. Evaporation of volatiles and crystallization of the residual solid from methanol-acetonitrile gave title compound as white prisms (1.61 g, 87%), m.p. 195–200° C.; 1H-NMR (DMSO-d6) δ 8.15 (s, 1H), 8.06 (s, 1H), 7.21 (br s, 2H), 6.15 and 5.95 (two m, 2H), 5.61 (m, 1H), 4.76 (t, J=5.4 Hz, 1H), 3.48 (t, J=5.5 Hz, 2H), 2.92 (m, 1H), 2.71 (m, 1H), 1.67 (m, 1H); [α]58920+4.5° (c 0.5, methanol).

Workup

customEvaporation of volatiles and crystallization of the residual solid from methanol-acetonitrile

Sources & evidence

ORD record: ord-dd59ce25b10f453d8d5969375326c6a8
Source dataset: uspto-grants-2006_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07115590B1

Reaction notes

Loading…