N-bromobutanimide → 8-Bromo-2-{[(1S)-1-methylpropyl]oxy}-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-amine

HRID 562738Notes

Reaction equation

[Br:1]N1C(=O)CCC1=O.[CH3:9][C@H:10]([O:13][C:14]1[N:22]=[C:21]2[C:17]([N:18]=[CH:19][N:20]2[CH:23]2[CH2:28][CH2:27][CH2:26][CH2:25][O:24]2)=[C:16]([NH2:29])[N:15]=1)[CH2:11][CH3:12]>C(Cl)(Cl)Cl>[Br:1][C:19]1[N:20]([CH:23]2[CH2:28][CH2:27][CH2:26][CH2:25][O:24]2)[C:21]2[C:17]([N:18]=1)=[C:16]([NH2:29])[N:15]=[C:14]([O:13][C@@H:10]([CH3:9])[CH2:11][CH3:12])[N:22]=2

Participants

Conditions

Temperature: 2.5 °C

Procedure

N-Bromosuccinimide (1.182 g, 6.64 mmol) was added portionwise to a solution of 2-{[(1S)-1-methylpropyl]oxy}-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-amine (1.935 g, 6.64 mmol) in chloroform (50 ml) at 0-5° C. The resulting green solution was stirred at 0-5° C. for 1 hour during which time it turned red and the mixture was then allowed to warm to room temperature and stirred overnight. The resulting green solution was washed with water (2×20 ml), separated using a hydrophobic frit and concentrated. The residue was dissolved in dichloromethane and purified by silica gel chromatography (100 g cartridge) using a Flashmaster II apparatus and a 0-100% ethyl acetate-cyclohexane gradient over 60 mins. The appropriate fractions were combined and evaporated in vacuo to give the title compound as a yellow foam (1.79 g).

Workup

temperatureto warm to room temperature
stirringstirred overnight
washThe resulting green solution was washed with water (2×20 ml)
customseparated
concentrationconcentrated
dissolutionThe residue was dissolved in dichloromethane
custompurified by silica gel chromatography (100 g cartridge)
waita 0-100% ethyl acetate-cyclohexane gradient over 60 mins
customevaporated in vacuo

Sources & evidence

ORD record: ord-d22616eb7306492fb479126db5031826
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08067426B2

Reaction notes

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