Diethyl ethylmalonate → 5-ethyl-6-hydroxy-2-phenyl-4(3H)-pyrimidinone

HRID 2400096Notes

Reaction equation

HRID 2400096 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-].[Na+].[CH2:15]([CH:17]([C:23](OCC)=[O:24])[C:18](OCC)=[O:19])[CH3:16]>CO>[CH2:15]([C:17]1[C:18](=[O:19])[NH:10][C:3]([C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=2)=[N:11][C:23]=1[OH:24])[CH3:16]

Participants

5

Reactant 3

HCID 8610Diethyl ethylmalonateHCID 10942334Sodium MethoxideHCID 16219042Benzamidine HCl hydrate

Product 1

HCID 196906695-ethyl-6-hydroxy-2-phenyl-4(3H)-pyrimidinoneYield 51%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A mixture of 45.19 g (0.29 mol) of benzamidine hydrochloride hydrate, 127.42 g (0.59 mol) of 25% sodium methoxide in methanol, 55 mL (0.29 mol) of diethyl ethylmalonate and 175 mL of methanol was heated at reflux for 25 h. The mixture was rotovapped to remove the bulk of the methanol. The residue was diluted with 300 mL of water and the pH was adjusted to 7 with concentrated hydrochloric acid. The solid precipitate was collected by filtration and dried under vacuum at 50° C. to afford 31.89 g (51%) of crude 5-ethyl-6-hydroxy-2-phenyl-4(3H)-pyrimidinone as a pale yellow solid. 1H-NMR (d6 -DMSO)δ1.05(3H, t), 2.39(2H,q), 7.5(3H,m), 8.1(2H,m).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 25 h
  3. customto remove the bulk of the methanol
  4. additionThe residue was diluted with 300 mL of water
  5. filtrationThe solid precipitate was collected by filtration
  6. customdried under vacuum at 50° C.

Sources & evidence

ORD record
ord-23045fbf3c0040abaacfefe32a7ccf08
Source dataset
uspto-grants-1995_09
Patent number
US05453414

Reaction notes

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