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

HRID 536017Notes

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.[Cl-].[CH:32]1([Zn+])[CH2:34][CH2:33]1>C(Cl)Cl.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>[CH:32]1([C:2]2[N:3]([CH2:28][CH2:29][CH3:30])[C:4](=[O:27])[C:5]3[NH:6][C:7]([C:11]4[CH:12]=[N:13][N:14]([CH2:16][C:17]5[CH:22]=[CH:21][CH:20]=[C:19]([C:23]([F:26])([F:25])[F:24])[CH:18]=5)[CH:15]=4)=[N:8][C:9]=3[N:10]=2)[CH2:34][CH2:33]1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 2-Chloro-1-propyl-8-[1-(3-trifluoromethyl-benzyl)-1H-pyrazol-4-yl]-1,7-dihydro-purin-6-one (prepared using same procedure as given in Example 2) (0.1 g, 0.23 mmol), Pd(PPh3)4 (0.319 g, 0.28 mmol) and cyclopropyl zinc chloride solution (10 ml, 0.5 M solution) were heated at 100° C. for 30 minutes. Reaction mixture was cooled, diluted with DCM (10 ml). Organic layer washed with brine (2×10 ml), dried over Na2SO4, evaporated and purified by preparative TLC to obtain pure 2-Cyclopropyl-1-propyl-8-[1-(3-trifluoromethyl-benzyl)-1H-pyrazol-4-yl]-1,7-dihydro-purin-6-one as white solid (23 mg, 23%)

Workup

customReaction mixture
temperaturewas cooled
washOrganic layer washed with brine (2×10 ml)
dry with materialdried over Na2SO4
customevaporated
custompurified by preparative TLC

Sources & evidence

ORD record: ord-b8be6d0008954133b70bb723bb5e9c02
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08859566B2

Reaction notes

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