Hydrochloric Acid → Ethyl pyrimidine-4-carboxylate

HRID 1155391Notes

Reaction equation

HRID 1155391 reaction equation
[O-]CC.[Na+].[C:5](OCC)(=O)[CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8].CS[C:18]1[N:19]=[CH:20]C2C(=O)OC(=O)N(C(C)C)C=2[N:32]=1.Cl>O>[CH2:10]([O:9][C:7]([C:6]1[N:32]=[CH:18][N:19]=[CH:20][CH:5]=1)=[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 13639438Ethyl pyrimidine-4-carboxylate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of sodium ethoxide (0.9 g. .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-4af851908bf8470eb31d3adb2a820cce
Source dataset
uspto-grants-1981_11
Patent number
US04301281

Reaction notes

Loading…