Sodium Hydroxide → HCID 67796978, compound

HRID 1534396Notes

Reaction equation

HRID 1534396 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.[CH:19]1([NH2:23])[CH2:22][CH2:21][CH2:20]1.[OH-].[Na+]>CO>[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:23][CH:19]2[CH2:22][CH2:21][CH2:20]2)[N:3]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 75645CyclobutylamineHCID 4514744-(2-Amino-6-chloro-9H-purin-9-yl)-2-cyclopentene-1-methanol, (1S,4R)-

Product 1

HCID 67796978HCID 67796978, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of (±)-cis-4-(2-Amino-6-chloro-9H-purin-9-yl)-2-cyclopentene-1-methanol from Example 4 (0.53 g 2 mmol) and cyclobutylamine (1.387 g, 19.5 mmol) in methanol (15 mL) was heated at 70°-75° C. (oil bath) for 29 hours. After cooling to room temperature, 2 mL of 1.0N NaOH was added. The solution was concentrated and the residue chromatographed on silica gel. Title compound was eluted with 5% methanol-chloroform as colourless foam which solidified to white powder in acetonitrile (454 mg, 75.7%), m.p. 181°-183° C.

Workup

  1. concentrationThe solution was concentrated
  2. customthe residue chromatographed on silica gel
  3. washTitle compound was eluted with 5% methanol-chloroform as colourless foam which

Sources & evidence

ORD record
ord-893bda86e82947828b560a2e99310203
Source dataset
uspto-grants-1992_02
Patent number
US05089500

Reaction notes

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