Reaction equation
C(O[C:4]([C:6]1[C:7]([NH:18][CH2:19][CH:20]=[CH2:21])=[N:8][C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[N:10][CH:11]=1)=[O:5])C.C([CH:24]([C:28](Cl)=[O:29])[C:25](Cl)=[O:26])C.O.Cl.[CH2:33]([O:35]CC)[CH3:34]>C(O)C>[CH2:33]([O:35][C:28]([C:24]1[C:25](=[O:26])[N:18]([CH2:19][CH:20]=[CH2:21])[C:7]2[N:8]=[C:9]([C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=3)[N:10]=[CH:11][C:6]=2[C:4]=1[OH:5])=[O:29])[CH3:34]Participants
7
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Procedure
To 16.3 g. (0.057 mole) of 4-(2-propenylamino)-2-phenyl-5-pyrimidine carboxylic acid ethyl ester in diethyl ether was added 4.3 g. (0.029 mole) of ethyl malonyl chloride and then stirred 3 hours at room temperature. The reaction was then filtered and stripped to dryness and the residue was added to a solution of 1.3 g. (0.057 mole) of Na in ethanol and stirred at room temperature for 10 minutes. Water was added until the reaction became clear and then acidified with HCl. This solution was chilled in ice and the resulting solid was removed by filtration. Recrystallization from ethyl acetate gave 0.55 g. of title product with m.p. 174°-175° C.
Workup
- filtrationThe reaction was then filtered
- additionthe residue was added to a solution of 1.3 g
- temperatureThis solution was chilled in ice
- customthe resulting solid was removed by filtration
- customRecrystallization from ethyl acetate
- customgave 0.55 g
Sources & evidence
- ORD record
- ord-2931fb7830f440c1a9f4234a75fb0dfb
- Source dataset
- uspto-grants-1981_03
- Patent number
- US04255568
Linked notes
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