Reaction equation
C(O[C:4]([C:6]1[C:7]([NH:18][CH2:19][CH3:20])=[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:23]([C:27](Cl)=[O:28])[C:24](Cl)=[O:25])C.[Na].[C:31](O)(=[O:33])[CH3:32]>C(OCC)C.C(O)C.O>[CH2:31]([O:33][C:27]([C:23]1[C:24](=[O:25])[N:18]([CH2:19][CH3:20])[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:28])[CH3:32]Participants
8
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Procedure
To 9.2 g. (0.034 mole) of 4-ethylamino-2-phenyl-5-pyrimidine-carboxylic acid ethyl ester in diethyl ether was added to 2.6 g. (0.017 mole) of ethyl malonyl chloride and then stirred 3 hours at room temperature. The reaction was then filtered and the filtrate stripped to dryness. This residue was dissolved in ethanol and added to a solution of 0.78 g. of sodium (0.034 mole) in ethanol and stirred at room temperature for 10 minutes. Acidification with acetic acid followed by the slow addition of water resulted in the formation of a precipitate. The crude product was removed by filtration and recrystallized from hexane m.p. 175°-177° C.--to give 1.0 g. of the title product.
Workup
- filtrationThe reaction was then filtered
- dissolutionThis residue was dissolved in ethanol
- additionadded to a solution of 0.78 g
- customresulted in the formation of a precipitate
- customThe crude product was removed by filtration
- customrecrystallized from hexane m.p. 175°-177° C.
- customto give 1.0 g
Sources & evidence
- ORD record
- ord-7a839cecf3a847daa7fceadecd52a48a
- Source dataset
- uspto-grants-1981_03
- Patent number
- US04255568
Linked notes
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