Benzoyl Peroxide → 8-bromomethyl-9-(2,2-dimethyl-propyl)-9H-purine-2-carbonitrile

HRID 271628Notes

Reaction equation

HRID 271628 reaction equation
[CH3:1][C:2]([CH3:17])([CH3:16])[CH2:3][N:4]1[C:12]([CH3:13])=[N:11][C:10]2[C:5]1=[N:6][C:7]([C:14]#[N:15])=[N:8][CH:9]=2.[Br:18]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:18][CH2:13][C:12]1[N:4]([CH2:3][C:2]([CH3:17])([CH3:16])[CH3:1])[C:5]2[C:10]([N:11]=1)=[CH:9][N:8]=[C:7]([C:14]#[N:15])[N:6]=2

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 179682149-(2,2-dimethyl-propyl)-8-methyl-9H-purine-2-carbonitrile

Product 1

HCID 179681638-bromomethyl-9-(2,2-dimethyl-propyl)-9H-purine-2-carbonitrile

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 1.1 g 9-(2,2-dimethyl-propyl)-8-methyl-9H-purine-2-carbonitrile, 1.7 g of N-bromosuccinimide and 116 mg dibenzoylperoxide was heated for 18 hours under reflux in 5 ml of CCl4. The mixture was evaporated and the residue was chromatographed on silicagel using hexanes/ethylacetate yielding 8-bromomethyl-9-(2,2-dimethyl-propyl)-9H-purine-2-carbonitrile as pale yellow wax.

Workup

  1. temperaturewas heated for 18 hours
  2. customThe mixture was evaporated
  3. customthe residue was chromatographed on silicagel

Sources & evidence

ORD record
ord-95a85bda824e4bb384af266a2c753a4a
Source dataset
uspto-grants-2008_11
Patent number
US07452886B2

Reaction notes

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