Water → HCID 67192387, compound

HRID 2401317Notes

Reaction equation

HRID 2401317 reaction equation
[CH:1]1([C:6]2[NH:14][C:13]3[C:12](=[O:15])[N:11]([CH2:16][CH2:17][CH3:18])[C:10](Cl)=[N:9][C:8]=3[N:7]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[NH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.O>CN1CCCC1=O>[CH:1]1([C:6]2[NH:14][C:13]3[C:12](=[O:15])[N:11]([CH2:16][CH2:17][CH3:18])[C:10]([NH:20][C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)=[N:9][C:8]=3[N:7]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 962WaterHCID 6115AnilineHCID 69937333HCID 69937333, compound

Product 1

HCID 67192387HCID 67192387, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
150 °C

Procedure

To a solution of 8-cyclopentyl-2-chloro-1-propyl-1,7-dihydro-purin-6-one (0.06 g, 0.21 mmol) in N-methyl-pyrrolidone (1 ml) was added aniline (0.20 g, 2.14 mmol) and the mixture was heated at 150° C. overnight. Water was added to the reaction mixture and the product was extracted with ethyl acetate. The ethyl acetate layer was dried over anhydrous sodium sulphate and concentrated under vacuum. The crude product was purified by preparative TLC using 5% methanol in dichloromethane to give the product (0.034 g, 47%) as a brown solid.

Workup

  1. extractionthe product was extracted with ethyl acetate
  2. dry with materialThe ethyl acetate layer was dried over anhydrous sodium sulphate
  3. concentrationconcentrated under vacuum
  4. customThe crude product was purified by preparative TLC

Sources & evidence

ORD record
ord-e76cdb3fcd604759bb7e1181dce6d9bf
Source dataset
uspto-grants-2014_08
Patent number
US08796290B2

Reaction notes

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