4-Aminopyrimidine → N-[(4-pyrimidinylcarbamoyl)amino]-1,2,3,6-tetrahydropyridine

HRID 2309184Notes

Reaction equation

HRID 2309184 reaction equation
O([C:8]([NH:10][N:11]1[CH2:16][CH:15]=[CH:14][CH2:13][CH2:12]1)=[O:9])C1C=CC=CC=1.[NH2:17][C:18]1[CH:23]=[CH:22][N:21]=[CH:20][N:19]=1>CN(C)C1C=CN=CC=1.ClCCCl>[N:21]1[CH:22]=[CH:23][C:18]([NH:17][C:8]([NH:10][N:11]2[CH2:16][CH:15]=[CH:14][CH2:13][CH2:12]2)=[O:9])=[N:19][CH:20]=1

Participants

5

Reactant 2

HCID 689584-AminopyrimidineHCID 20152376N-(phenoxycarbonylamino)-1,2,3,6-tetrahydropyridine

Product 1

HCID 20185943N-[(4-pyrimidinylcarbamoyl)amino]-1,2,3,6-tetrahydropyridineYield 64.4%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 111,2-DichloroethaneSolvent

Procedure

A mixture of N-(phenoxycarbonylamino)-1,2,3,6-tetrahydropyridine (2.61 g), 4-aminopyrimidine (0.95 g) and 4-dimethylaminopyridine (1.83 g) in 1,2-dichloroethane (80 ml) was refluxed for 2.5 hours. The reaction mixture was evaporated to dryness. The crude residue was dissolved in ethyl acetate (50 ml) and washed with water (50 ml), and then extracted with 5% hydrochloric acid (30 ml×2). The extract was neutralized with sodium bicarbonate and further extracted with chloroform (30 ml×2). The chloroform layer was washed with water (50 ml), dried over magnesium sulfate and evaporated to give N-[(4-pyrimidinylcarbamoyl)amino]-1,2,3,6-tetrahydropyridine (1.41 g), which was recrystallized from ethyl acetate.

Workup

  1. temperaturewas refluxed for 2.5 hours
  2. customThe reaction mixture was evaporated to dryness
  3. dissolutionThe crude residue was dissolved in ethyl acetate (50 ml)
  4. washwashed with water (50 ml)
  5. extractionextracted with 5% hydrochloric acid (30 ml×2)
  6. extractionfurther extracted with chloroform (30 ml×2)
  7. washThe chloroform layer was washed with water (50 ml)
  8. dry with materialdried over magnesium sulfate
  9. customevaporated

Sources & evidence

ORD record
ord-b49baaf970a04e19854b2ada8e8cbee2
Source dataset
uspto-grants-1987_09
Patent number
US04694004

Reaction notes

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