Acetic Acid → 8-Ethyl-7,8-dihydro-5-hydroxy-7-oxo-2-phenylpyrido[2,3-d]pyrimidine-6-carboxylic acid ethyl ester

HRID 225325Notes

Reaction equation

HRID 225325 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

HCID 176Acetic AcidHCID 5360545SodiumHCID 109209242-Ethylpropanedioyl dichlorideHCID 127840724-Ethylamino-2-phenyl-5-pyrimidine-carboxylic acid ethyl ester

Product 1

HCID 547318648-Ethyl-7,8-dihydro-5-hydroxy-7-oxo-2-phenylpyrido[2,3-d]pyrimidine-6-carboxylic acid ethyl ester

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolvent

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

  1. filtrationThe reaction was then filtered
  2. dissolutionThis residue was dissolved in ethanol
  3. additionadded to a solution of 0.78 g
  4. customresulted in the formation of a precipitate
  5. customThe crude product was removed by filtration
  6. customrecrystallized from hexane m. p. 175°-177° C.
  7. customto give 1.0 g

Sources & evidence

ORD record
ord-a16a24a85a9d41489876d8dc501d91d8
Source dataset
uspto-grants-1980_11
Patent number
US04236004

Reaction notes

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