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

HRID 1443

Reaction equation

HRID 1443 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) δ 1.05(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-28a790364d3a4b39a6924f5c3d8fb5d8
Source dataset
uspto-grants-1998_03
Patent number
US05726124

Linked notes

Loading…