1-(3-Pyridyl)-3-(dimethylamino)-2-propen-1-one → N-(4-Methoxyphenyl)-4-(pyridin-3-yl)pyrimidin-2-amine

HRID 2352160Notes

Reaction equation

HRID 2352160 reaction equation
CN(C)[CH:3]=[CH:4][C:5]([C:7]1[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=1)=O.C(=O)(O)O.[CH3:18][O:19][C:20]1[CH:25]=[CH:24][C:23]([NH:26][C:27]([NH2:29])=[NH:28])=[CH:22][CH:21]=1>C(O)(C)C>[CH3:18][O:19][C:20]1[CH:21]=[CH:22][C:23]([NH:26][C:27]2[N:29]=[C:5]([C:7]3[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=3)[CH:4]=[CH:3][N:28]=2)=[CH:24][CH:25]=1

Participants

4

Reactant 2

HCID 5670331-(3-Pyridyl)-3-(dimethylamino)-2-propen-1-oneHCID 178492308HCID 178492308, compound

Product 1

HCID 14346975N-(4-Methoxyphenyl)-4-(pyridin-3-yl)pyrimidin-2-amine

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of 14.4 g of 3-dimethylamino-1-(3-pyridinyl)-2-propen-1-one and 16.1 g of 4-methoxyphenyl guanidine carbonate in 200 ml of isopropanol was heated at reflux for 20 hours. The reaction mixture was cooled, the crude product was collected by filtration and washed with water. The material was recrystallized from isopropanol to give the desired product as light yellow crystals, mp 121°-122° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 20 hours
  3. temperatureThe reaction mixture was cooled
  4. filtrationthe crude product was collected by filtration
  5. washwashed with water
  6. customThe material was recrystallized from isopropanol

Sources & evidence

ORD record
ord-06b60842b9e140c999eac6875efd072d
Source dataset
uspto-grants-1989_10
Patent number
US04876252

Reaction notes

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