Sodium Hydroxide → (+/-)-cis-4-(2-Amino-6-((2-hydroxy-1-(hydroxymethyl)ethyl)amino)-9H-purin-9-yl)-2-cyclopentene-1-methanol

HRID 728664

Reaction equation

Cl.[NH2:2][CH:3]([CH2:6][OH:7])[CH2:4][OH:5].[NH2:8][C:9]1[N:17]=[C:16]2[C:12]([N:13]=[CH:14][N:15]2[C@@H:18]2[CH2:22][C@H:21]([CH2:23][OH:24])[CH:20]=[CH:19]2)=[C:11](Cl)[N:10]=1.[OH-].[Na+]>CO>[NH2:8][C:9]1[N:17]=[C:16]2[C:12]([N:13]=[CH:14][N:15]2[C@@H:18]2[CH2:22][C@H:21]([CH2:23][OH:24])[CH:20]=[CH:19]2)=[C:11]([NH:2][CH:3]([CH2:6][OH:7])[CH2:4][OH:5])[N:10]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A solution of serinol hydrochloride (0.765 g, 6.00 mmol) in methanol (20 mL) was stirred with basic ion exchange resin for 10 minutes. The resin was filtered off and the filtrate concentrated to a colorless oil. To this was added (±)-cis-4-(2-amino-6-chloro-9H-purin-9-yl)-2-cyclopentene-1-methanol (0.544 g, 2.00 mmol) and methanol (10 mL). The resulting solution was stirred in a Parr bomb at 80° C. overnight. 1N NaOH (2 mL) was added and the solvent evaporated. The residue was chromatrographed on silica gel. Title compound eluted with 20% methanol-chloroform; white powder after crystallization from acetonitrile-methanol (0.404 g, 63%), m.p. 160-162° C.

Workup

filtrationThe resin was filtered off
concentrationthe filtrate concentrated to a colorless oil
customthe solvent evaporated
washTitle compound eluted with 20% methanol-chloroform
customwhite powder after crystallization from acetonitrile-methanol (0.404 g, 63%), m.p. 160-162° C.

Sources & evidence

ORD record: ord-e235de0dbce9486f8b16ceb6b86aa1a9
Source dataset: uspto-grants-1991_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05049671

Linked notes

Loading…