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

HRID 224720Notes

Reaction equation

HRID 224720 reaction equation
[O-]CC.[Na+].[C:5]([O:13]CC)(=O)[CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8].[CH3:16][S:17][C:18]1[N:19]=[CH:20][C:21]2[C:26](=O)[O:25]C(=O)[N:23]([CH:29]([CH3:31])[CH3:30])[C:22]=2[N:32]=1.Cl>O>[CH2:10]([O:9][C:7]([C:6]1[C:5](=[O:13])[N:23]([CH:29]([CH3:30])[CH3:31])[C:22]2[N:32]=[C:18]([S:17][CH3:16])[N:19]=[CH:20][C:21]=2[C:26]=1[OH:25])=[O:8])[CH3:11]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7761Diethyl MalonateHCID 2723922Sodium ethoxideHCID 205620621-isopropyl-7-(methylthio)-1H-pyrimido[4,5-d][1,3]oxazine-2,4-dione

Product 1

HCID 54729310Ethyl 5-hydroxy-8-isopropyl-2-(methylthio)-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidine-6-carboxylate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of sodium ethoxide (0.9 g. 0.039 g. atom of sodium in 75 ml. of ethanol) was added 6.24 g. (0.03 mole) of diethyl malonate. The ethanol was removed in a rotary evaporator. To the residue was added 100 ml. of dimethyl formamide followed by 3.3 g. (0.013 mole) of 7-methylthio-1-isopropyl-2H-pyrimido[4,5-d][1,3]oxazine-2,4(1H)-dione. The reaction mixture was heated under reflux for 1 hour, cooled in ice and poured into 400 ml. of water. The solution was acidified with conc. hydrochloric acid and the resulting product was collected by suction filtration. Recrystallization from ethanol gave 2 g. of product--m.p. 138°-140° C.

Workup

  1. customThe ethanol was removed in a rotary evaporator
  2. additionTo the residue was added 100 ml
  3. temperatureThe reaction mixture was heated
  4. temperatureunder reflux for 1 hour
  5. temperaturecooled in ice
  6. additionpoured into 400 ml
  7. filtrationthe resulting product was collected by suction filtration
  8. customRecrystallization from ethanol
  9. customgave 2 g

Sources & evidence

ORD record
ord-0a7863497f5c46b097dc1f792b769003
Source dataset
uspto-grants-1980_11
Patent number
US04233446

Reaction notes

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