Sodium Hydroxide → HCID 178501564, compound

HRID 2354847Notes

Reaction equation

[CH2:1]([N:8]1[C:16](Br)=[N:15][C:14]2[C:9]1=[N:10][C:11]([NH:19][CH2:20][C:21]([O:23][CH3:24])=[O:22])=[N:12][C:13]=2[NH2:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-:25].[Na+]>Cl>[CH2:1]([N:8]1[C:16]([OH:25])=[N:15][C:14]2[C:9]1=[N:10][C:11]([NH:19][CH2:20][C:21]([O:23][CH3:24])=[O:22])=[N:12][C:13]=2[NH2:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 100 °C

Procedure

Thus obtained 9-benzyl-8-bromo-2-methoxycarbonylmethylaminoadenine was added to concentrated hydrochloric acid (10 ml), and the mixture was stirred for 8 hours at 100° C. The mixture was neutralized in an ice bath with 5% sodium hydroxide solution (pH 7) and the solvent was removed. To the residue were added methanol (30 ml) and sulfuric acid (1 ml), and the mixture was refluxed for 4 hours. After being neutralized (pH 6) in an ice bath with saturated sodium hydrogencarbonate solution, the solution was extracted with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate, and concentrated. The residue was purified by column chromatography and the obtained compound was washed with methanol to give the captioned compound (0.02 g) as a white solid.

Workup

customthe solvent was removed
additionTo the residue were added methanol (30 ml) and sulfuric acid (1 ml)
temperaturethe mixture was refluxed for 4 hours
extractionthe solution was extracted with dichloromethane
dry with materialThe organic layer was dried over anhydrous magnesium sulfate
concentrationconcentrated
customThe residue was purified by column chromatography
washthe obtained compound was washed with methanol

Sources & evidence

ORD record: ord-9a3788aaad924509b6c30d6bb6f4d016
Source dataset: uspto-grants-2010_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07754728B2

Reaction notes

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