1-Bromo-2-methylpropane → HCID 67194473, compound

HRID 2401313Notes

Reaction equation

HRID 2401313 reaction equation
[Cl:1][C:2]1[NH:3][C:4](=[O:24])[C:5]2[N:6]([CH2:16][O:17][CH2:18][CH2:19][Si:20]([CH3:23])([CH3:22])[CH3:21])[C:7]([CH:11]3[CH2:15][CH2:14][CH2:13][CH2:12]3)=[N:8][C:9]=2[N:10]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:31](Br)[CH:32]([CH3:34])[CH3:33]>CN(C=O)C.O>[Cl:1][C:2]1[N:3]([CH2:31][CH:32]([CH3:34])[CH3:33])[C:4](=[O:24])[C:5]2[N:6]([CH2:16][O:17][CH2:18][CH2:19][Si:20]([CH3:21])([CH3:23])[CH3:22])[C:7]([CH:11]3[CH2:12][CH2:13][CH2:14][CH2:15]3)=[N:8][C:9]=2[N:10]=1

Participants

6

Reactant 3

HCID 65551-Bromo-2-methylpropaneHCID 10796Cesium carbonateHCID 136350313HCID 136350313, compound

Product 1

HCID 67194473HCID 67194473, compoundYield 69.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A mixture 2-chloro-8-cyclopentyl-7-(2-trimethylsilanyl-ethoxymethyl)-1,7-dihydro-purin-6-one (0.1 g, 0.27 mmol) and cesium carbonate (0.1 g, 0.30 mmol) was taken in DMF (2 ml) and isobutyl bromide (0.055 g, 0.41 mmol) was added drop wise. The reaction mixture was stirred and heated at 60° C. overnight, diluted with water (10 ml). The aqueous layer was extracted with ethyl acetate. The organic layer was washed with saturated brine solution, dried over sodium sulphate and concentrated. The residue was purified by column chromatography to provide 2-chloro-8-cyclopentyl-1-isobutyl-7-(2-trimethylsilanyl-ethoxymethyl)-1,7-dihydro-purin-6-one (0.08 g, 69%) as yellow oil.

Workup

  1. extractionThe aqueous layer was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine solution
  3. dry with materialdried over sodium sulphate
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-353b9007938941d48fe988b90e235cff
Source dataset
uspto-grants-2014_08
Patent number
US08796290B2

Reaction notes

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