Chloroform → 1-(2-Cyanoethylamino)-5-(4,6-dimethyl-2-pyrimidylamino)pentane

HRID 34753

Reaction equation

HRID 34753 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[N:5]=[C:4]([NH:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][NH2:15])[N:3]=1.[C:16](#[N:19])[CH:17]=[CH2:18].C(Cl)(Cl)Cl>C(O)(C)(C)C>[C:16]([CH2:17][CH2:18][NH:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][NH:9][C:4]1[N:5]=[C:6]([CH3:8])[CH:7]=[C:2]([CH3:1])[N:3]=1)#[N:19]

Participants

5

Reactant 3

HCID 6212ChloroformHCID 7855AcrylonitrileHCID 143460175-(4,6-Dimethyl-2-pyrimidylamino)-1-pentanamine

Product 1

HCID 143460181-(2-Cyanoethylamino)-5-(4,6-dimethyl-2-pyrimidylamino)pentaneYield 85.8%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent2×

Procedure

To a stirred solution of (XII) (966 mg) in t-butanol was added 250 mg of acrylonitrile dissolved in 1 ml t-butanol over a period of 1 hour. Continued stirring for 3.5 hours at room temperature and finally refluxed for 1.5 hours. Chloroform was added and the product was extracted into 1N H2SO4. The aqueous phase was washed once with CHCl3, then basified to pH 10 with 2N NaOH and the free amine extracted into CHCl3. The product (XIII) 1.04 g was obtained by evaporation of the solvents under vacuum.

Workup

  1. temperaturefinally refluxed for 1.5 hours
  2. extractionthe product was extracted into 1N H2SO4
  3. washThe aqueous phase was washed once with CHCl3
  4. extractionthe free amine extracted into CHCl3

Sources & evidence

ORD record
ord-910574ed73dc41d5b4fcb1ab0f5d4a28
Source dataset
uspto-grants-1988_08
Patent number
US04762949

Linked notes

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