Dimethylformamide → 2-Chloro-7-methyl-1-propyl-8-[1-(3-trifluoromethyl-benzyl)-1H-pyrazol-4-yl]-1,7-dihydro-purin-6-one

HRID 925577Notes

Reaction equation

HRID 925577 reaction equation
[Cl:1][C:2]1[N:3]([CH2:28][CH2:29][CH3:30])[C:4](=[O:27])[C:5]2[NH:6][C:7]([C:11]3[CH:12]=[N:13][N:14]([CH2:16][C:17]4[CH:22]=[CH:21][CH:20]=[C:19]([C:23]([F:26])([F:25])[F:24])[CH:18]=4)[CH:15]=3)=[N:8][C:9]=2[N:10]=1.[C:31]([O-])([O-])=O.[K+].[K+].CI.CN(C=O)C>O>[Cl:1][C:2]1[N:3]([CH2:28][CH2:29][CH3:30])[C:4](=[O:27])[C:5]2[N:6]([CH3:31])[C:7]([C:11]3[CH:12]=[N:13][N:14]([CH2:16][C:17]4[CH:22]=[CH:21][CH:20]=[C:19]([C:23]([F:26])([F:25])[F:24])[CH:18]=4)[CH:15]=3)=[N:8][C:9]=2[N:10]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 668032942-Chloro-1-propyl-8-[1-(3-trifluoromethyl-benzyl)-1H-pyrazol-4-yl]-1,7-dihydro-purin-6-one

Product 1

HCID 671350852-Chloro-7-methyl-1-propyl-8-[1-(3-trifluoromethyl-benzyl)-1H-pyrazol-4-yl]-1,7-dihydro-purin-6-oneYield 58%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 2-Chloro-1-propyl-8-[1-(3-trifluoromethyl-benzyl)-1H-pyrazol-4-yl]-1,7-dihydro-purin-6-one (200 mg, 0.46 mmol), K2CO3 (95 mg, 0.69 mmol), MeI (85 mg, 0.60 mmol) and DMF (2 ml) were stirred at 60° C. for 2 hours. Reaction mixture was cooled, diluted with water (10 ml) and extracted with ethyl acetate (2×5 ml). The organic layer was washed with brine (2×10 ml), dried over Na2SO4 and evaporated to obtain 2-Chloro-7-methyl-1-propyl-8-[1-(3-trifluoromethyl-benzyl)-1H-pyrazol-4-yl]-1,7-dihydro-purin-6-one (120 mg, 58%)

Workup

  1. customReaction mixture
  2. temperaturewas cooled
  3. extractionextracted with ethyl acetate (2×5 ml)
  4. washThe organic layer was washed with brine (2×10 ml)
  5. dry with materialdried over Na2SO4
  6. customevaporated

Sources & evidence

ORD record
ord-baab88508c4c43e4b91cf162006eece0
Source dataset
uspto-grants-2016_03
Patent number
US09284316B2

Reaction notes

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