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

HRID 536018Notes

Reaction equation

HRID 536018 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-e64827e634234863bcd220dce7ca24fe
Source dataset
uspto-grants-2014_10
Patent number
US08859566B2

Reaction notes

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