Water → HCID 22249949, compound

HRID 890216Notes

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% ethylacetate/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% ethylacetate/hexane)

Sources & evidence

ORD record: ord-4dc97098b691442284755f4d575c7d1e
Source dataset: uspto-grants-2006_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06995163B2

Reaction notes

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