Dimethyl Sulfoxide → 6-Ethoxy-2-phenylpyrimidin-4(3H)-one

HRID 1463234Notes

Reaction equation

HRID 1463234 reaction equation
O.Cl.[C:3]([NH2:11])(=[NH:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.C([O-])(=O)C.[Na+].[CH2:17]([O:19][C:20](OCC)=[CH:21][C:22](OCC)=[O:23])[CH3:18].CS(C)=O>[OH-].[Na+]>[CH2:17]([O:19][C:20]1[N:11]=[C:3]([C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=2)[NH:10][C:22](=[O:23])[CH:21]=1)[CH3:18]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 1693882-Propenoic acid, 3,3-diethoxy-, ethyl esterHCID 517045Sodium AcetateHCID 16219042Benzamidine HCl hydrate

Product 1

HCID 6084316-Ethoxy-2-phenylpyrimidin-4(3H)-oneYield 57%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 3.14 g (20.0 mmol) of benzamidine hydrochloride hydrate, 1.65 g (20.1 mmol) of powdered anhydrous sodium acetate, 4.17 g (22.2 mmol) of ethyl 3,3-diethoxyacrylate and 10 mL of DMSO was heated at 120° C. for 8 h. The mixture was cooled, diluted with 50 mL of 5% aqueous NaOH and washed with two 100 mL portions of ether. The aqueous layer was acidified with concentrated hydrochloric acid and the precipitate was collected by filtration and dried under vacuum at 50° C. to furnish 2.28 g (57%) of crude 6-ethoxy-2-phenyl-4(3H)-pyrimidinone as a yellow solid 1H-NMR (d6-DMSO) δ1.35(3H,t), 4.33(2H,q), 5.60(1H,s), 7.50(3H,m), 8.2(2H,m).

Workup

  1. temperatureThe mixture was cooled
  2. washwashed with two 100 mL portions of ether
  3. filtrationthe precipitate was collected by filtration
  4. customdried under vacuum at 50° C.

Sources & evidence

ORD record
ord-17711c91b7784461abcde2829759fd38
Source dataset
uspto-grants-1994_04
Patent number
US05300477

Reaction notes

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