(+)-(1R,4S)-4-(6-Amino-9H-purin-9-yl)-2-cyclopentene-1-methanol (1R,4S)-4-(6-Chloro-9H-purin-9-yl)-2-cyclopentene-1-methanol → [(1R,4S)-4-(6-aminopurin-9-yl)cyclopent-2-en-1-yl]methanol

HRID 986926Notes

Reaction equation

HRID 986926 reaction equation
ClC1N=CN=C2C=1N=CN2[C@H]1C[C@@H](CO)C=C1.[NH2:18][C:19]1[N:27]=[CH:26][N:25]=[C:24]2[C:20]=1[N:21]=[CH:22][N:23]2[C@H:28]1[CH2:32][C@@H:31]([CH2:33][OH:34])[CH:30]=[CH:29]1>N>[NH2:18][C:19]1[N:27]=[CH:26][N:25]=[C:24]2[C:20]=1[N:21]=[CH:22][N:23]2[C@H:28]1[CH2:32][C@@H:31]([CH2:33][OH:34])[CH:30]=[CH:29]1

Participants

3

Reactant 1

HCID 86759193(+)-(1R,4S)-4-(6-Amino-9H-purin-9-yl)-2-cyclopentene-1-methanol (1R,4S)-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%

Reagents, catalysts & solvents 1

HCID 222AmmoniaSolvent

Procedure

(+)-(1R,4S)-4-(6-Amino-9H-purin-9-yl)-2-cyclopentene-1-methanol (1R,4S)-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]589+4.5° (c 0.5, methanol).

Workup

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

Sources & evidence

ORD record
ord-c99fb9b24e314f19b623ffa977d11ffa
Source dataset
uspto-grants-2003_10
Patent number
US06630477B1

Reaction notes

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