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

HRID 1443

반응식

HRID 1443 반응식
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]

참가 물질

5

반응물 3

HCID 8610Diethyl ethylmalonateHCID 10942334Sodium MethoxideHCID 16219042Benzamidine HCl hydrate

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매2회

실험 절차

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).

후처리

  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.

출처 및 근거

ORD 기록
ord-28a790364d3a4b39a6924f5c3d8fb5d8
출처 데이터셋
uspto-grants-1998_03
특허 번호
US05726124

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