Hydrochloric Acid → Ethyl 8-allyl-5-hydroxy-7-oxo-2-phenyl-7,8-dihydropyrido[2,3-d]pyrimidine-6-carboxylate

HRID 127378Notes

Reaction equation

HRID 127378 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:19]1[C:24]2[N:25]=[C:26]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[N:27]=[CH:28][C:23]=2[C:22](=O)[O:21]C1=O)[CH:17]=[CH2:18].Cl>CN(C=O)C>[CH2:10]([O:9][C:7]([C:6]1[C:5](=[O:13])[N:19]([CH2:16][CH:17]=[CH2:18])[C:24]2[N:25]=[C:26]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[N:27]=[CH:28][C:23]=2[C:22]=1[OH:21])=[O:8])[CH3:11]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7761Diethyl MalonateHCID 2723922Sodium ethoxideHCID 205620631-allyl-7-phenyl-1H-pyrimido[4,5-d][1,3]oxazine-2,4-dione

Product 1

HCID 54726500Ethyl 8-allyl-5-hydroxy-7-oxo-2-phenyl-7,8-dihydropyrido[2,3-d]pyrimidine-6-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a 50 ml. solution of NaOEt (0.3 g. Na-0.013 mole) was added 2.08 g. (0.013 mole) of diethyl malonate and this was stirred 10 minutes, then stripped to dryness. DMF was added to form a solution and then 1.85 g. (0.0065 mole) of 1-(2-propenyl)-7-phenyl-2H-pyrimido[4,5-d][1,3]oxazine-2,4(1H)-dione was added and heated at reflux for 1.5 hours. When cool, the reaction was poured into dilute HCl and the resulting precipitate collected on a filter and rinsed with water. Recrystallization from ethyl acetate gave 1.0 g. of product--m.p. 177°-180° C.

Workup

  1. customto form a solution
  2. temperatureheated
  3. temperatureat reflux for 1.5 hours
  4. temperatureWhen cool
  5. customthe resulting precipitate collected on
  6. filtrationa filter
  7. washrinsed with water
  8. customRecrystallization from ethyl acetate
  9. customgave 1.0 g

Sources & evidence

ORD record
ord-0343e8fffa0845b192ccd7cf48335e57
Source dataset
uspto-grants-1981_03
Patent number
US04255568

Reaction notes

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