Hexane → 5-Bromo-4-isobutylamino-pyrimidine-2-carbonitrile

HRID 271590Notes

Reaction equation

HRID 271590 reaction equation
[Br:1][C:2]1[C:3]([NH:9][CH2:10][CH:11]([CH3:13])[CH3:12])=[N:4][C:5](Cl)=[N:6][CH:7]=1.[C-:14]#[N:15].[K+].C1(C)C=CC(S(O)(=O)=O)=CC=1.[Na].CCCCCC>CS(C)=O.CCOC(C)=O>[Br:1][C:2]1[C:3]([NH:9][CH2:10][CH:11]([CH3:13])[CH3:12])=[N:4][C:5]([C:14]#[N:15])=[N:6][CH:7]=1

Participants

7

Reactant 4

HCID 8058HexaneHCID 9032Potassium CyanideHCID 17968203(5-Bromo-2-chloro-pyrimidin-4-yl)-isobutyl-amineHCID 24195884Sodium p-toluenesulfonate

Product 1

HCID 179682615-Bromo-4-isobutylamino-pyrimidine-2-carbonitrileYield 84%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
75 °C

Procedure

To a solution of (5-bromo-2-chloro-pyrimidin-4-yl)-isobutyl-amine (11.2 mmol) in DMSO (30 ml) is added potassium cyanide (22.5 mmol) and sodium p-toluenesulfonic acid (3.75 mmol) in DMSO(17 ml) at room temperature. The mixture is stirred at 75° C. for 18 h 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:AcOEt=25:1, 15:1 and 12:1) gives the product in 84% yield. Rf=46 (n-hexane:AcOEt=3:1)

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:AcOEt=25:1, 15:1 and 12:1) gives the product in 84% yield

Sources & evidence

ORD record
ord-d5b69e0d3c3f4b868f3baa2ff1438108
Source dataset
uspto-grants-2008_11
Patent number
US07452886B2

Reaction notes

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