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

HRID 225334Notes

Reaction equation

HRID 225334 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-420aae89895c42aa9d792e1ba4051346
Source dataset
uspto-grants-1980_11
Patent number
US04236004

Reaction notes

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