Tetrahydrofuran → 1-Propyl-8-[1-(3-trifluoromethyl-benzyl)-1H-pyrazol-4-yl]-2-(4-trifluoromethyl-phenyl)-1,7-dihydro-purin-6-one

HRID 925565Notes

Reaction equation

HRID 925565 reaction equation
Cl[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.[F:31][C:32]([F:43])([F:42])[C:33]1C=CC(B(O)O)=C[CH:34]=1.C([O-])(O)=O.[Na+].[CH2:49]1[CH2:53]O[CH2:51][CH2:50]1>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:28]([N:3]1[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]=[C:2]1[C:49]1[CH:50]=[CH:51][C:33]([C:32]([F:43])([F:42])[F:31])=[CH:34][CH:53]=1)[CH2:29][CH3:30]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 516892Sodium BicarbonateHCID 27343894-(Trifluoromethyl)phenylboronic acidHCID 668032942-Chloro-1-propyl-8-[1-(3-trifluoromethyl-benzyl)-1H-pyrazol-4-yl]-1,7-dihydro-purin-6-one

Product 1

HCID 469132741-Propyl-8-[1-(3-trifluoromethyl-benzyl)-1H-pyrazol-4-yl]-2-(4-trifluoromethyl-phenyl)-1,7-dihydro-purin-6-oneYield 36%

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Procedure

A mixture of 2-Chloro-1-propyl-8-[1-(3-trifluoromethyl-benzyl)-1H-pyrazol-4-yl]-1,7-dihydro-purin-6-one (0.1 g, 0.239 mmol) and 4-Trifluoromethylphenyl boronic acid (0.038 g, 0.239 mmol) in THF (5 ml) were stirred at room temperature under argon and added 1M aqueous NaHCO3 (0.04 g, 0.478 mmol) and Pd(PPh3)4 (0.013 g, 0.0119 mmol). The reaction mixture was heated at 80° C. for overnight and the solvent was removed under reduced pressure. The residue was purified by column chromatography to obtain 1-Propyl-8-[1-(3-trifluoromethyl-benzyl)-1H-pyrazol-4-yl]-2-(4-trifluoromethyl-phenyl)-1,7-dihydro-purin-6-one (0.05 g, 36%) as a white solid.

Workup

  1. temperatureThe reaction mixture was heated at 80° C. for overnight
  2. customthe solvent was removed under reduced pressure
  3. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-c7633e8f9ccb40d989c12252c41ed6d0
Source dataset
uspto-grants-2016_03
Patent number
US09284316B2

Reaction notes

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