Water → (4-chloro-phenyl)-[2-(3,5-dimethyl-pyrazol-1-yl)-9-methyl-9H-purin-6-yl]-carbamic acid 2-methoxy-ethyl ester

HRID 2386598Notes

Reaction equation

HRID 2386598 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[N:17]=[C:16]([N:18]3[C:22]([CH3:23])=[CH:21][C:20]([CH3:24])=[N:19]3)[N:15]=[C:14]3[C:10]=2[N:11]=[CH:12][N:13]3[CH3:25])=[CH:4][CH:3]=1.[H-].[Na+].Cl[C:29]([O:31][CH2:32][CH2:33][O:34][CH3:35])=[O:30].O>CN(C)C=O>[CH3:35][O:34][CH2:33][CH2:32][O:31][C:29](=[O:30])[N:8]([C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=1)[C:9]1[N:17]=[C:16]([N:18]2[C:22]([CH3:23])=[CH:21][C:20]([CH3:24])=[N:19]2)[N:15]=[C:14]2[C:10]=1[N:11]=[CH:12][N:13]2[CH3:25]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 694002-Methoxyethyl chloroformateHCID 44472568NS13001

Product 1

HCID 45110733(4-chloro-phenyl)-[2-(3,5-dimethyl-pyrazol-1-yl)-9-methyl-9H-purin-6-yl]-carbamic acid 2-methoxy-ethyl esterYield 42%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(4-Chloro-phenyl)-[2-(3,5-dimethyl-pyrazol-1-yl)-9-methyl-9H-purin-6-yl]-amine (520 mg, 1.5 mmol) was dissolved in N,N-dimethylformamide (5 mL). Sodium hydride (60% in mineral oil, 90 mg, 2.2 mmol) was added and mixture was stirred at room temperature for 30 minutes. 2-Methoxyethyl chloroformate (0.26 mL, 2.2 mmol) was added and stirring was continued at room temperature over night. Water was added and the aqueous phase was extracted twice with ethyl acetate. The combined organic phases were dried over magnesium sulphate, filtrated and concentrated in vacuo. The crude product was purified by flash chromatography (ethyl acetate/methanol as eluent) to give (4-chloro-phenyl)-[2-(3,5-dimethyl-pyrazol-1-yl)-9-methyl-9H-purin-6-yl]-carbamic acid 2-methoxy-ethyl ester (280 mg, 42%) as a white solid.

Workup

  1. stirringstirring
  2. waitwas continued at room temperature over night
  3. extractionthe aqueous phase was extracted twice with ethyl acetate
  4. dry with materialThe combined organic phases were dried over magnesium sulphate
  5. filtrationfiltrated
  6. concentrationconcentrated in vacuo
  7. customThe crude product was purified by flash chromatography (ethyl acetate/methanol as eluent)

Sources & evidence

ORD record
ord-3574bf4097ca425188029db6d9e3c79d
Source dataset
uspto-grants-2012_09
Patent number
US08268838B2

Reaction notes

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