2-chloro-7H-purine → (2-(Cyclopentylamino)-6-[(2,2-diphenylethyl)amino]-9H-purin-9-yl]-1-deoxy-N-ethyl-beta-D-ribofuranuronamide

HRID 582540Notes

Reaction equation

[C:1]1([CH:7]([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[CH2:8][NH:9][C:10]2[N:18]=[C:17]([NH:19][C@@H:20]3[CH2:24][CH2:23][CH2:22][C@H:21]3O)[N:16]=[C:15]3[C:11]=2[N:12]=[CH:13][N:14]3[C@@H:26]2[O:32][C@H:31]([C:33]([NH:35][CH2:36][CH3:37])=[O:34])[C@@H:29]([OH:30])[C@H:27]2[OH:28])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.ClC1N=C2C(NC=N2)=CN=1>>[CH:20]1([NH:19][C:17]2[N:16]=[C:15]3[C:11]([N:12]=[CH:13][N:14]3[C@@H:26]3[O:32][C@H:31]([C:33]([NH:35][CH2:36][CH3:37])=[O:34])[C@@H:29]([OH:30])[C@H:27]3[OH:28])=[C:10]([NH:9][CH2:8][CH:7]([C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)[C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[N:18]=2)[CH2:21][CH2:22][CH2:23][CH2:24]1

Participants

Reactant 2

HCID 5193142-chloro-7H-purine

HCID 44352986(1R-trans)-1-deoxy-1-[6-[(2,2-diphenylethyl)amino]-2-[(2-hydroxycyclopentyl)amino]-9H-purin-9-yl]-N-ethyl-beta-D-ribofuranuronamide

Product 1

HCID 44352987(2-(Cyclopentylamino)-6-[(2,2-diphenylethyl)amino]-9H-purin-9-yl]-1-deoxy-N-ethyl-beta-D-ribofuranuronamide

Procedure

(1R-trans)-1-deoxy-1-[6-[(2,2-diphenylethyl)amino]-2-[(2-hydroxycyclopentyl)amino]-9H-purin-9-yl]-N-ethyl-β-D-ribofuranuronamide, from the 2-chloropurine (0.35 g) and (R)-(trans)-2-aminocyclopentanol1 (1.0 g) at 130° C. for 10h. The product was purified on silica eluting with ethyl acetate:methanol 19:1 and then on silica eluting with dichloromethane:methanol:0.880 ammonia (100:8:1). The product had m.p. 122 to 130° C. Analysis found C,62.6, H,6.2, N,16.2%; C31H37N7O5.0.4H2O requires C,62.6, H,6.4, N,16.5%.

Workup

customThe product was purified on silica eluting with ethyl acetate:methanol 19:1

Sources & evidence

ORD record: ord-091c72eff0f345ab8efd577878cf4649
Source dataset: uspto-grants-1999_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05925624

Reaction notes

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