Water → 8-Bromo-2-(cyclobutyloxy)-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-amine

HRID 527812Notes

Reaction equation

HRID 527812 reaction equation
[Br:1]N1C(=O)CCC1=O.[CH:9]1([O:13][C:14]2[N:22]=[C:21]3[C:17]([N:18]=[CH:19][N:20]3[CH:23]3[CH2:28][CH2:27][CH2:26][CH2:25][O:24]3)=[C:16]([NH2:29])[N:15]=2)[CH2:12][CH2:11][CH2:10]1.O>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][CH:9]1[CH2:12][CH2:11][CH2:10]1)[N:22]=2

Participants

5

Reactant 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 592526272-(Cyclobutyloxy)-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-amine

Product 1

HCID 592526428-Bromo-2-(cyclobutyloxy)-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-amineYield 112.8%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

N-Bromosuccinimide (1.152 g, 6.47 mmol) was added to a stirred solution of 2-(cyclobutyloxy)-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-amine (1.248 g, 4.31 mmol) in chloroform (15 ml) at 0° C. The mixture was warmed to room temperature and left overnight when water (15 ml) was added and the phases separated. The aqueous layer was extracted with dichloromethane and the organic extracts were combined, washed with brine, dried over anhydrous magnesium sulphate and evaporated to give the title compound as an orange foam (1.79 g).

Workup

  1. additionwas added
  2. customthe phases separated
  3. extractionThe aqueous layer was extracted with dichloromethane
  4. washwashed with brine
  5. dry with materialdried over anhydrous magnesium sulphate
  6. customevaporated

Sources & evidence

ORD record
ord-e255f50efe38462b9c5ac680fa674c06
Source dataset
uspto-grants-2016_05
Patent number
US09346806B2

Reaction notes

Loading…