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

HRID 2082726Notes

Reaction equation

HRID 2082726 reaction equation
[Na].COS(O)(=O)=O.[CH2:8]([O:11][C:12]1[CH:20]=[CH:19][CH:18]=[CH:17][C:13]=1[C:14]([NH2:16])=[NH:15])[CH2:9][CH3:10].C([O:23][CH:24]=[C:25]([C:31](OCC)=O)[C:26]([O:28][CH2:29][CH3:30])=[O:27])C.O>C(O)C.C(O)(=O)C>[O:23]=[C:24]1[NH:16][C:14]([C:13]2[CH:17]=[CH:18][CH:19]=[CH:20][C:12]=2[O:11][CH2:8][CH2:9][CH3:10])=[N:15][CH:31]=[C:25]1[C:26]([O:28][CH2:29][CH3:30])=[O:27]

Participants

7

Reactant 4

HCID 962WaterHCID 6871Diethyl (ethoxymethylene)malonateHCID 5360545SodiumHCID 86734867n-Propoxybenzamidine methyl sulfate

Product 1

HCID 12535801Ethyl 1,6-dihydro-6-oxo-2-(2-propoxyphenyl)pyrimidine-5-carboxylateYield 78.5%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 702EthanolSolvent2×

Procedure

To a warm solution of sodium (181.7 g., 7.9 g-atoms) in ethanol (5 l) was added with stirring a slurry of 2-n-propoxybenzamidine methyl sulfate (1146.7 g., 3.95 moles) in ethanol 1.6 l). After 2-3 minutes diethyl ethoxymethylenemalonate 854 g., 3.95 moles) was added and the mixture stirred and heated under reflux for 2.25 hours. The mixture was cooled and then added to cold water (13 l). The mixture was acidified to pH 5-6 with glacial acetic acid. The solid was collected by filtration, washed with water, and dried to give the title compound (937.8 g.), m.p. 102°-104°. An additional crop of product (101.6 g., m.p. 105°-107°, was obtained from the filtrate and washings. Total yield of product, 1039.4 g. (87%).

Workup

  1. addition, 3.95 moles) was added
  2. temperatureheated
  3. temperatureunder reflux for 2.25 hours
  4. temperatureThe mixture was cooled
  5. filtrationThe solid was collected by filtration
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-065927c40061460988df48a29522d551
Source dataset
uspto-grants-1978_04
Patent number
US04082751

Reaction notes

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