Dimethylformamide → HCID 9930135, compound

HRID 842063Notes

Reaction equation

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

Participants

Conditions

Temperature: 0 °C

Procedure

to a mixture of about 60% sodium hydride (oily) (1.4 g) and dimethylformamide (70 ml) is added 7,9-dihydro-9-methyl-2-pheny-8H-purin-8-one (7.0 g) in portions at 0-5° C., and the mixture is stirred at 0° C. for one hour. To the mixture is added dropwise 2-bromo-N-ethyl-N-phenylacetamide (8.3 g) at the same temperature. After the addition, the mixture is stirred at room temperature for three hours. To the reaction mixture are added water and chloroform. The chloroform layer is separated, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue is purified by silica gel column chromatography (eluent; chloroform) and recrystallized from ethanol to give the desired compound (10.3 g).

Workup

additionAfter the addition
stirringthe mixture is stirred at room temperature for three hours
customThe chloroform layer is separated
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated under reduced pressure
customThe residue is purified by silica gel column chromatography (eluent; chloroform)
customrecrystallized from ethanol

Sources & evidence

ORD record: ord-7e00407432a94475bfc5223a8ea82788
Source dataset: uspto-grants-2002_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06372740B1

Reaction notes

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