Cyclopentylamine → HCID 70369950, compound

HRID 1087033Notes

Reaction equation

HRID 1087033 reaction equation
[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[C@@H:11]2[CH2:15][C@H:14]([CH2:16][OH:17])[CH:13]=[CH:12]2)=[C:4](Cl)[N:3]=1.C(N(CC)CC)C.[CH:26]1([NH2:31])[CH2:30][CH2:29][CH2:28][CH2:27]1.[OH-].[Na+]>C(O)C>[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[C@@H:11]2[CH2:15][C@H:14]([CH2:16][OH:17])[CH:13]=[CH:12]2)=[C:4]([NH:31][CH:26]2[CH2:30][CH2:29][CH2:28][CH2:27]2)[N:3]=1

Participants

6

Reactant 4

HCID 2906CyclopentylamineHCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 4514744-(2-Amino-6-chloro-9H-purin-9-yl)-2-cyclopentene-1-methanol, (1S,4R)-

Product 1

HCID 70369950HCID 70369950, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of (±)-cis-4-(-2-Amino-6-chloro-9H-purin-9-yl)-2-cyclopentene-1-methanol (0.53 g, 2 mmol) from Example 4, triethylamine (2.00 g, 20 mmol), cyclopentylamine (267 mg, 3.1 mmol) and ethanol (10 mL) was stirred at reflux for 9 hours. The solution was allowed to cool to room temperature before the addition of 2 mL of 1.0N NaOH. Concentration of the solution afforded the crude product which was purified by elution from a silica gel column using 5% methanol in chloroform (0.430 g, 68.4%). Crystallization of such a sample from ethanol-acetonitrile gave an off-white powder, m.p. 143°-146° C.

Workup

  1. temperatureat reflux for 9 hours

Sources & evidence

ORD record
ord-814274ff26054d6097f722520abe2290
Source dataset
uspto-grants-1991_07
Patent number
US05034394

Reaction notes

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