Water → HCID 22249949, compound

HRID 966039Notes

Reaction equation

[H-].[Na+].[CH2:3]([CH:5]([N:8]1[C:16](=[O:17])[NH:15][C:14]2[C:13]([CH3:18])=[N:12][C:11]3=[C:19]([C:23]4[C:28]([CH3:29])=[CH:27][C:26]([CH3:30])=[CH:25][C:24]=4[CH3:31])[C:20]([CH3:22])=[N:21][N:10]3[C:9]1=2)[CH2:6][CH3:7])[CH3:4].[CH2:32](Br)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.O>CN(C)C=O>[CH2:32]([N:15]1[C:14]2[C:13]([CH3:18])=[N:12][C:11]3=[C:19]([C:23]4[C:24]([CH3:31])=[CH:25][C:26]([CH3:30])=[CH:27][C:28]=4[CH3:29])[C:20]([CH3:22])=[N:21][N:10]3[C:9]=2[N:8]([CH:5]([CH2:6][CH3:7])[CH2:3][CH3:4])[C:16]1=[O:17])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

Participants

Conditions

Temperature: 70 °C

Procedure

Sodium hydride (28 mg, 0.71 mmol) was added to a solution of 1-(1-ethylpropyl)-6-mesityl-4,7-dimethyl-2,3-dihydro-1H-pyrazolo[5,1-b]purin-2-one (230 mg, 0.59 mmol) in N,N-dimethylformamide (5 mL) at room temperature. After 30 minutes, benzyl bromide (0.079 mL, 0.65 mmol) was added, followed by stirring at 70° C. for one hour. Water was added under ice-cooling, followed by extracting with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and evaporated. The residue was purified by silica gel column chromatography (15-20% ethyl acetate/hexane) to give the title compound (259 mg) as brown crystals.

Workup

temperaturecooling
extractionby extracting with ethyl acetate
washThe organic layer was washed with brine
dry with materialdried over anhydrous magnesium sulfate
customevaporated
customThe residue was purified by silica gel column chromatography (15-20% ethyl acetate/hexane)

Sources & evidence

ORD record: ord-78ae9ee71d294c9fa3241ddca147931d
Source dataset: uspto-grants-2005_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06951865B2

Reaction notes

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