3,5-Dimethylpyrazole → NS13001

HRID 1809234Notes

Reaction equation

HRID 1809234 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-60692faa83c64a36b5da477516039f9a
Source dataset
uspto-grants-2013_01
Patent number
US08362024B2

Reaction notes

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