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

HRID 225331Notes

Reaction equation

HRID 225331 reaction equation
CC[O-].[Na+].[C:5]([O:11][CH2:12][CH3:13])(=[O:10])[CH2:6][C:7]([O-])=[O:8].[CH3:14][O:15][CH2:16][CH2:17][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.Cl>>[CH2:12]([O:11][C:5]([C:6]1[C:7](=[O:8])[N:18]([CH2:17][CH2:16][O:15][CH3:14])[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:10])[CH3:13]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 2723922Sodium ethoxideHCID 3595298Propanedioic acid, monoethyl esterHCID 205620581-(2-methoxyethyl)-7-phenyl-1H-pyrimido[4,5-d][1,3]oxazine-2,4-dione

Product 1

HCID 54727901Ethyl 5-hydroxy-8-(2-methoxyethyl)-7-oxo-2-phenyl-7,8-dihydropyrido[2,3-d]pyrimidine-6-carboxylate

Procedure

50 ml. of NaOEt (0.5 g. Na--0.021 mole) was added to 3.4 g. (0.021 mole) of ethyl malonate and stirred 10 minutes, then evaporated to dryness. DMF was added until a solution was achieved and then 3.2 g. (0.011 mole) of 1-(2-methoxyethyl)-7-phenyl-2H-pyrimido[4,5-d][1,3]oxazine-2,4(1H)-dione was added and this mixture refluxed 2 hours. The chilled reaction was poured into dilute HCl and the ensuing precipitate filtered off and rinsed with water. Recrystallization from ethyl acetate gave 3.5 g. of the title product--m.p. 178°-179° C.

Workup

  1. customevaporated to dryness
  2. additionDMF was added until a solution
  3. temperaturethis mixture refluxed 2 hours
  4. customThe chilled reaction
  5. filtrationthe ensuing precipitate filtered off
  6. washrinsed with water
  7. customRecrystallization from ethyl acetate
  8. customgave 3.5 g

Sources & evidence

ORD record
ord-2b070e37622048cca380428a28b520fa
Source dataset
uspto-grants-1980_11
Patent number
US04236004

Reaction notes

Loading…