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

HRID 536027Notes

Reaction equation

[CH3:1][OH:2].[H-].[Na+].Cl[C:6]1[N:7]([CH2:32][CH2:33][CH3:34])[C:8](=[O:31])[C:9]2[NH:10][C:11]([C:15]3[CH:16]=[N:17][N:18]([CH2:20][C:21]4[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([F:30])([F:29])[F:28])[CH:22]=4)[CH:19]=3)=[N:12][C:13]=2[N:14]=1>C(OCC)(=O)C>[CH3:1][O:2][C:6]1[N:7]([CH2:32][CH2:33][CH3:34])[C:8](=[O:31])[C:9]2[NH:10][C:11]([C:15]3[CH:16]=[N:17][N:18]([CH2:20][C:21]4[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([F:30])([F:29])[F:28])[CH:22]=4)[CH:19]=3)=[N:12][C:13]=2[N:14]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To the mixture of methanol (2 ml) and NaH (45 mg, 1.1 mmol), 2-Chloro-1-propyl-8-[1-(3-trifluoromethyl-benzyl)-1H-pyrazol-4-yl]-1,7-dihydro-purin-6-one (50 mg, 0.11 mmol) was added and refluxed for 2 hours at 80° C. Reaction mixture was cooled, diluted with ethyl acetate (10 ml) and quenched with saturated NH4Cl solution. The organic layer was separated and washed with brine (2×10 ml), dried over Na2SO4, filtered and evaporated. The residue obtained was purified by preparative HPLC to obtain pure 2-Methoxy-1-propyl-8-[1-(3-trifluoromethyl-benzyl)-1H-pyrazol-4-yl]-1,7-dihydro-purin-6-one (26 mg, 53%) as an off white solid.

Workup

additionwas added
customReaction mixture
temperaturewas cooled
customquenched with saturated NH4Cl solution
customThe organic layer was separated
washwashed with brine (2×10 ml)
dry with materialdried over Na2SO4
filtrationfiltered
customevaporated
customThe residue obtained
customwas purified by preparative HPLC

Sources & evidence

ORD record: ord-68e7bf5fb7cd4587a506b3fdf2062dd1
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08859566B2

Reaction notes

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