Sodium hydride → HCID 468290, compound

HRID 728652Notes

Reaction equation

[H-].[Na+].[NH2:3][C:4]1[N:12]=[C:11]2[C:7]([N:8]=[CH:9][N:10]2[C@@H:13]2[CH2:17][C@H:16]([CH2:18][OH:19])[CH:15]=[CH:14]2)=[C:6](Cl)[N:5]=1>>[NH2:3][C:4]1[N:12]=[C:11]2[C:7]([N:8]=[CH:9][N:10]2[C@@H:13]2[CH2:17][C@H:16]([CH2:18][OH:19])[CH:15]=[CH:14]2)=[C:6]([O:19][CH2:18][CH2:16][CH3:15])[N:5]=1

Participants

Reactant 2

HCID 24758Sodium hydride

HCID 4514744-(2-Amino-6-chloro-9H-purin-9-yl)-2-cyclopentene-1-methanol, (1S,4R)-

Product 1

HCID 468290HCID 468290, compound

Conditions

Temperature: 80 °C

Procedure

A flask was charged with sodium hydride (60% oil dispersion 158 m8, 3 mMol) which was then washed with hexanes before the addition of n-propanol (25 mL). (±)-cis-4-(2-Amino-6-chloro-9H-purin-9-yl)-2-cyclopentene-1-methanol from Example 4 (400 mg, 1.5 mmol) was added and the solution was stirred at 80° C. for 2 hours and the neutralized by the addition of 1.0 N HC1. Concentration of the solution afforded the crude product which was purified by elution from a silica gel column with 2% methanol-chloroform (350 mg, 81%). Crystallization of such a sample from ethanol-water gave an off-white powder, m.p. 97-99° C.

Workup

washwas then washed with hexanes before the addition of n-propanol (25 mL)
additionthe neutralized by the addition of 1.0 N HC1

Sources & evidence

ORD record: ord-46f8e552cee54a2887e2536d7aeff9f3
Source dataset: uspto-grants-1991_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05049671

Reaction notes

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