Bicarbonate Ion → (Pyrimidin-4-yl)acetonitrile

HRID 547443Notes

Reaction equation

HRID 547443 reaction equation
C[N:2](C)/[CH:3]=[CH:4]/[C:5]1[CH:10]=[CH:9][N:8]=[CH:7][N:6]=1.NOS(O)(=O)=O.C(=O)([O-])O>>[N:8]1[CH:9]=[CH:10][C:5]([CH2:4][C:3]#[N:2])=[N:6][CH:7]=1

Participants

4

Reactant 3

HCID 769Bicarbonate IonHCID 76284hydroxylamine-O-sulfonic acidHCID 6433770Ethenamine, N,N-dimethyl-2-(4-pyrimidinyl)- (9CI)

Product 1

HCID 14169572(Pyrimidin-4-yl)acetonitrileYield 39.1%

Conditions

Temperature
50 °C

Procedure

To 70 mL of an aqueous solution containing 5 g of dimethyl-[(E)-2-(4-pyrimidinyl)vinyl]amine, 9.48 g of hydroxylamine-O-sulfonic acid was added and stirred at 50° C. for 30 minutes. The reaction solution was made basic by addition of saturated aqueous hydrogen-carbonate solution under cooling with ice, and extracted with ethyl acetate. The ethyl acetate extract was dried over anhydrous magnesium sulfate and removed of the solvent by distillation under reduced pressure. Thus obtained residue was purified on 30 g silica gel column chromatography (eluent, chloroform:methanol=30:1) to provide 1.56 g (yield: 39%) of the title compound as pale yellow crystal.

Workup

  1. additionwas added
  2. temperatureunder cooling with ice
  3. extractionextracted with ethyl acetate
  4. extractionThe ethyl acetate extract
  5. dry with materialwas dried over anhydrous magnesium sulfate
  6. customremoved of the solvent by distillation under reduced pressure
  7. customThus obtained residue was purified on 30 g silica gel column chromatography (eluent, chloroform:methanol=30:1)

Sources & evidence

ORD record
ord-f28b9423104643fd87633d8be6a244eb
Source dataset
uspto-grants-2011_05
Patent number
US07939536B2

Reaction notes

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