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

HRID 224711Notes

Reaction equation

HRID 224711 reaction equation
CC[O-].[Na+].[C:5]([O:11][CH2:12][CH3:13])(=[O:10])[CH2:6][C:7]([O-])=[O:8].[C:14]1([C:20]2[N:21]=[CH:22][C:23]3[C:28](=O)[O:27]C(=O)[N:25]([CH2:31][CH2:32][CH3:33])[C:24]=3[N:34]=2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.Cl>>[CH2:12]([O:11][C:5]([C:6]1[C:7](=[O:8])[N:25]([CH2:31][CH2:32][CH3:33])[C:24]2[N:34]=[C:20]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[N:21]=[CH:22][C:23]=2[C:28]=1[OH:27])=[O:10])[CH3:13]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 2723922Sodium ethoxideHCID 3595298Propanedioic acid, monoethyl esterHCID 205620477-Phenyl-1-propyl-2H-pyrimido[4,5-d][1,3]oxazine-2,4(1H)-dione

Product 1

HCID 54729615Ethyl 5-hydroxy-7-oxo-2-phenyl-8-propyl-7,8-dihydropyrido[2,3-d]pyrimidine-6-carboxylate

Procedure

50 ml. of NaOEt (0.24 g.-0.011 mole) was added to 1.7 g. (0.011 mole) of ethyl malonate and stirred 10 minutes, then evaporated to dryness. DMF was added until a solution formed and 1.5 g. (0.005 mole) of 7-phenyl-1-propyl-2H-pyrimido[4,5-d][1,3]oxazine-2,4(1H)-dione was added and the mixture refluxed 2 hours. The chilled reaction was poured into dilute HCl and the resulting precipitate filtered off and rinsed with water. Recrystallization from ethyl acetate gave 1.5 g. of the title compound--m.p. 164°-167° C.

Workup

  1. customevaporated to dryness
  2. additionDMF was added until a solution
  3. customformed
  4. temperaturethe mixture refluxed 2 hours
  5. customThe chilled reaction
  6. filtrationthe resulting precipitate filtered off
  7. washrinsed with water
  8. customRecrystallization from ethyl acetate
  9. customgave 1.5 g

Sources & evidence

ORD record
ord-c94e9f5ba74548ccb2fff16a96e46e52
Source dataset
uspto-grants-1980_11
Patent number
US04233446

Reaction notes

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