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

HRID 1155376Notes

Reaction equation

HRID 1155376 reaction equation
CC[O-].[Na+].[C:5]([O:13]CC)(=O)[CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8].[CH2:16]([N:18]1[C:23]2[N:24]=[C:25]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[N:26]=[CH:27][C:22]=2[C:21](=O)[O:20]C1=O)[CH3:17].Cl>CN(C)C=O>[CH2:10]([O:9][C:7]([C:6]1[C:5](=[O:13])[N:18]([CH2:16][CH3:17])[C:23]2[N:24]=[C:25]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[N:26]=[CH:27][C:22]=2[C:21]=1[OH:20])=[O:8])[CH3:11]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7761Diethyl MalonateHCID 2723922Sodium ethoxideHCID 205620651-ethyl-7-phenyl-2H-pyrimido[4,5-d][1,3]oxazine-2,4(1H)-dione

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 1

HCID 6228DimethylformamideSolvent

Procedure

To a 40 ml. solution of NaOEt (1.0 g. Na-0.042 mole) was added 6.8 g. (0.042 mole) of diethyl malonate and this is stirred 10 minutes, then stripped to dryness. Dimethylformamide was added until a solution formed and to this was added 5.7 g. (0.021 mole) of 1-ethyl-7-phenyl-2H-pyrimido[4,5-d][1,3]oxazine-2,4(1H)-dione and the mixture heated at reflux for 2 hours. The reaction was then cooled and poured into dilute HCl and the resulting precipitate filtered off and rinsed well with water. Recrystallization with hexane-ethyl acetate gave 5.1 g. of the title product--m.p. 177°-180° C.

Workup

  1. customformed
  2. additionto this was added 5.7 g
  3. temperatureat reflux for 2 hours
  4. temperatureThe reaction was then cooled
  5. filtrationthe resulting precipitate filtered off
  6. washrinsed well with water
  7. customRecrystallization with hexane-ethyl acetate
  8. customgave 5.1 g

Sources & evidence

ORD record
ord-7931343bccbe4fdf8e24027edaa73fe9
Source dataset
uspto-grants-1981_11
Patent number
US04301281

Reaction notes

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