Water → 8-Bromo-2-[(2-cyclopropylethyl)oxy]-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-amine

HRID 1011056Notes

Reaction equation

HRID 1011056 reaction equation
[CH:1]1([CH2:4][CH2:5][O:6][C:7]2[N:15]=[C:14]3[C:10]([N:11]=[CH:12][N:13]3[CH:16]3[CH2:21][CH2:20][CH2:19][CH2:18][O:17]3)=[C:9]([NH2:22])[N:8]=2)[CH2:3][CH2:2]1.[Br:23]N1C(=O)CCC1=O.O>C(Cl)(Cl)Cl>[Br:23][C:12]1[N:13]([CH:16]2[CH2:21][CH2:20][CH2:19][CH2:18][O:17]2)[C:14]2[C:10]([N:11]=1)=[C:9]([NH2:22])[N:8]=[C:7]([O:6][CH2:5][CH2:4][CH:1]1[CH2:2][CH2:3]1)[N:15]=2

Participants

5

Reactant 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 576996002-[(2-Cyclopropylethyl)oxy]-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-amine

Product 1

HCID 576996678-Bromo-2-[(2-cyclopropylethyl)oxy]-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-amine

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To an ice cooled stirring solution of 2-[(2-cyclopropylethyl)oxy]-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-amine (6.53 g) in chloroform (75 ml), was added N-bromosuccinimide (4.02 g). The reaction mixture was allowed to warm to room temperature and after 16 h treated with water and extracted twice with DCM. The combined extracts were washed with dilute sodium metabisulphite then dilute brine, dried by passing through a hydrophobic frit and evaporated to give the title compound as an orange foam, yield 7.96 gm.

Workup

  1. extractionextracted twice with DCM
  2. washThe combined extracts were washed with dilute sodium metabisulphite
  3. dry with materialdilute brine, dried
  4. customevaporated

Sources & evidence

ORD record
ord-95c04acf6b8a4b6faaea0ab5a773f362
Source dataset
uspto-grants-2011_07
Patent number
US07977344B2

Reaction notes

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