3,5-Dimethylpyrazole → NS13001

HRID 524512Notes

Reaction equation

HRID 524512 reaction equation
[H-].[Na+].[CH3:3][C:4]1[CH:8]=[C:7]([CH3:9])[NH:6][N:5]=1.CN(C)C=O.Cl[C:16]1[N:24]=[C:23]2[C:19]([N:20]=[CH:21][N:22]2[CH3:25])=[C:18]([NH:26][C:27]2[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][CH:28]=2)[N:17]=1>O>[Cl:33][C:30]1[CH:29]=[CH:28][C:27]([NH:26][C:18]2[N:17]=[C:16]([N:5]3[C:4]([CH3:3])=[CH:8][C:7]([CH3:9])=[N:6]3)[N:24]=[C:23]3[C:19]=2[N:20]=[CH:21][N:22]3[CH3:25])=[CH:32][CH:31]=1

Participants

6

Reactant 4

HCID 62103,5-DimethylpyrazoleHCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 592936372-Chloro-N-(4-chlorophenyl)-9-methyl-9H-purin-6-amine

Product 1

HCID 44472568NS13001Yield 13.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

Sodium hydride (60% in mineral oil, 160 mg, 4.1 mmol) was added to 3,5-dimethylpyrazole (320 mg, 3.4 mmol) dissolved N,N-dimethylformamide (10 mL) and the mixture was stirred for 30 min. (2-Chloro-9-methyl-9H-purin-6-yl)-(4-chloro-phenyl)amine (1.0 g 3.40 mmol) was added and the reaction mixture was heated at 120° C. for 4 days, cooled down and poured into water. The aqueous phase was extracted with ethyl acetate. The combined organic phases were dried over magnesium sulphate, filtered and concentrated in vacuo. The crude product was purified by flash chromatography (dichloromethane/methanol/ammonia) to give (4-chloro-phenyl)-[2-(3,5-dimethyl-pyrazol-1-yl)-9-methyl-9H-purin-6-yl]-amine (160 mg, 13%) as a yellow crystalline compound.

Workup

  1. additionwas added
  2. temperaturecooled down
  3. extractionThe aqueous phase was extracted with ethyl acetate
  4. dry with materialThe combined organic phases were dried over magnesium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude product was purified by flash chromatography (dichloromethane/methanol/ammonia)

Sources & evidence

ORD record
ord-0d5a01cf826442e6872b8227d4fb6eb4
Source dataset
uspto-grants-2016_05
Patent number
US09340544B2

Reaction notes

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