2-Propen-1-one, 3-(dimethylamino)-1-(4-pyridinyl)- → N-(4-Methoxyphenyl)-4-(4-pyridinyl)-2-pyrimidinamine

HRID 2352161Notes

Reaction equation

HRID 2352161 reaction equation
CN(C)[CH:3]=[CH:4][C:5]([C:7]1[CH:12]=[CH:11][N:10]=[CH:9][CH:8]=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:12]=[CH:11][N:10]=[CH:9][CH:8]=3)[CH:4]=[CH:3][N:28]=2)=[CH:24][CH:25]=1

Participants

4

Reactant 2

HCID 7145312-Propen-1-one, 3-(dimethylamino)-1-(4-pyridinyl)-HCID 178492308HCID 178492308, compound

Product 1

HCID 14346980N-(4-Methoxyphenyl)-4-(4-pyridinyl)-2-pyrimidinamine

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A 14.4 g amount of 3-dimethylamino-1-(4-pyridinyl)-2-propen-1-one (U.S. Pat. No. 4,281,000) and 16.1 g of 4-methoxyphenylguanidine carbonate in 200 ml of isopropanol was heated at reflux for 24 hours. The solvent was evaporated to 1/3 volume, then the mixture was cooled in an ice-bath to crystallize the crude product. The product was collected by filtration and washed with water, then with isopropanol. The material was recrystallized from isopropanol/ethylene glycol monomethyl ether to give 16.7 g of the desired product as yellow crystals, mp 174°-175° C.

Workup

  1. temperatureat reflux for 24 hours
  2. customThe solvent was evaporated to 1/3 volume
  3. temperaturethe mixture was cooled in an ice-bath
  4. customto crystallize the crude product
  5. filtrationThe product was collected by filtration
  6. washwashed with water
  7. customThe material was recrystallized from isopropanol/ethylene glycol monomethyl ether

Sources & evidence

ORD record
ord-401a9c241a2949e18d5a587eb2230ef0
Source dataset
uspto-grants-1989_10
Patent number
US04876252

Reaction notes

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