Reaction equation
[Br:1]N1C(=O)CCC1=O.[CH:9]1([O:15][C:16]2[N:24]=[C:23]3[C:19]([N:20]=[CH:21][N:22]3[CH:25]3[CH2:30][CH2:29][CH2:28][CH2:27][O:26]3)=[C:18]([NH2:31])[N:17]=2)[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1.O>C(Cl)(Cl)Cl>[Br:1][C:21]1[N:22]([CH:25]2[CH2:30][CH2:29][CH2:28][CH2:27][O:26]2)[C:23]2[C:19]([N:20]=1)=[C:18]([NH2:31])[N:17]=[C:16]([O:15][CH:9]1[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14]1)[N:24]=2Participants
5
Procedure
N-Bromosuccinimide (0.214 g, 1.2 mmol) was added to a stirred solution of 2-(cyclohexyloxy)-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-amine (0.254 g, 0.80 mmol) in chloroform (5 ml) at 0° C. The resultant mixture was stirred at 0° C. for 1.5 hours and then warmed to room temperature and stirred for a further 2 hours. Water (5 ml) was added and the phases separated using a hydrophobic frit. The organic phase was evaporated and the residue dissolved in dichloromethane and purified on a 70 g aminopropyl (NH2) cartridge eluting with a 0-100% ethyl acetate in cyclohexane gradient over 40 mins. The appropriate fractions were combined and evaporated in vacuo to give the title compound as a white solid (0.252 g).
Workup
- customthe phases separated
- customThe organic phase was evaporated
- dissolutionthe residue dissolved in dichloromethane
- custompurified on a 70 g aminopropyl (NH2) cartridge
- washeluting with a 0-100% ethyl acetate in cyclohexane gradient over 40 mins
- customevaporated in vacuo
Sources & evidence
- ORD record
- ord-1622cb2406e8427c9d8b5b881c1f9053
- Source dataset
- uspto-grants-2011_11
- Patent number
- US08067426B2
Linked notes
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