Isobutylamine → (5-Bromo-2-chloro-pyrimidin-4-yl)-isobutyl-amine

HRID 271589Notes

Reaction equation

HRID 271589 reaction equation
[Br:1][C:2]1[C:3](Cl)=[N:4][C:5]([Cl:8])=[N:6][CH:7]=1.[CH2:10]([NH2:14])[CH:11]([CH3:13])[CH3:12].CCCCCC>CO.CCOC(C)=O>[Br:1][C:2]1[C:3]([NH:14][CH2:10][CH:11]([CH3:13])[CH3:12])=[N:4][C:5]([Cl:8])=[N:6][CH:7]=1

Participants

6

Reactant 3

HCID 6558IsobutylamineHCID 8058HexaneHCID 2899735-Bromo-2,4-dichloropyrimidine

Product 1

HCID 17968203(5-Bromo-2-chloro-pyrimidin-4-yl)-isobutyl-amineYield 78%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

To a solution of 5-bromo-2,4-dichloropyrimidine (14.0 mmol) in methanol (30 ml) is added isobutylamine (28.0 mmol) at room temperature. The mixture is stirred at room temperature for one day and diluted with AcOEt. The organic layer is washed with water and brine, dried over sodium sulfate and concentrated. Chromatography on silica gel (n-hexane and n-hexane:AcOEt=25:1) gives the product in 78% yield. Rf=0.52 (n-hexane:AcOEt=4:1)

Workup

  1. washThe organic layer is washed with water and brine
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated
  4. customChromatography on silica gel (n-hexane and n-hexane:AcOEt=25:1) gives the product in 78% yield

Sources & evidence

ORD record
ord-92d83aee66944604aa0b6ee00fe41e5a
Source dataset
uspto-grants-2008_11
Patent number
US07452886B2

Reaction notes

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