Hydrochloric Acid → Ethyl 1,6-dihydro-6-oxo-2-(2-propoxyphenyl)pyrimidine-5-carboxylate

HRID 2082725Notes

Reaction equation

HRID 2082725 reaction equation
Cl.[CH2:2]([O:5][C:6]1[CH:14]=[CH:13][CH:12]=[CH:11][C:7]=1[C:8]([NH2:10])=[NH:9])[CH2:3][CH3:4].[Na].C([O:18][CH:19]=[C:20]([C:26](OCC)=O)[C:21]([O:23][CH2:24][CH3:25])=[O:22])C.Cl>C(O)C>[O:18]=[C:19]1[NH:10][C:8]([C:7]2[CH:11]=[CH:12][CH:13]=[CH:14][C:6]=2[O:5][CH2:2][CH2:3][CH3:4])=[N:9][CH:26]=[C:20]1[C:21]([O:23][CH2:24][CH3:25])=[O:22]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6871Diethyl (ethoxymethylene)malonateHCID 5360545SodiumHCID 122542252-Propyloxybenzamidine Hydrochloride

Product 1

HCID 12535801Ethyl 1,6-dihydro-6-oxo-2-(2-propoxyphenyl)pyrimidine-5-carboxylateYield 96%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

2-Propoxybenzamidine hydrochloride (12.0 g., 0.0558 mole) was added to a stirred, cooled (ice-water) solution of sodium (2.57 g., 0.112 g-atom) in ethanol (50 ml.). To this cooled, stirred solution was added a solution of diethyl ethoxymethylenemalonate (12.1 g., 0.0558 mole) in ethanol (50 ml.) during 10 minutes. The mixture was heated under reflux for 2.5 hours. The cooled solution was poured onto ice and acidified with 6N hydrochloric acid. The precipitated ethyl 1,6-dihydro-6-oxo-2-(2-n-propoxyphenyl)pyrimidine-5-carboxylate (16.2 g., 96% yield) had m.p. 111°-113°. Two recrystallizations from cyclohexane gave title product with m.p. 112°-113°.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 2.5 hours
  3. additionThe cooled solution was poured onto ice

Sources & evidence

ORD record
ord-542b9b7cc677492a9d32173b7cb97703
Source dataset
uspto-grants-1978_04
Patent number
US04082751

Reaction notes

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