Ethyl 3-oxo-4-phenylbutanoate → 2,6-dibenzyl-1H-pyrimidin-4-one

HRID 1729236

반응식

HRID 1729236 반응식
[Na].Cl.[C:3]1([CH2:9][C:10]([NH2:12])=[NH:11])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[C:13]1([CH2:19][C:20](=O)[CH2:21][C:22](OCC)=[O:23])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C(O)C>[C:3]1([CH2:9][C:10]2[N:12]=[C:20]([CH2:19][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH:21]=[C:22]([OH:23])[N:11]=2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

참가 물질

5

반응물 3

HCID 225855Ethyl 3-oxo-4-phenylbutanoateHCID 5360545SodiumHCID 124155142-Phenylethanimidamide hydrochloride

생성물 1

HCID 1785158572,6-dibenzyl-1H-pyrimidin-4-one수율 34.3%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

To a solution of sodium (1.84 g, 80 mmol) in ethanol (200 ml) was added phenylacetamidine hydrochloride (16.2 g, 95.0 mmol) and ethyl 4-phenylacetoacetate (15 g, 72.9 mmol). The mixture was heated under reflux with stirring for 5 days followed by cooling and evaporation in vacuo. Water (150 ml) was added to the residue causing a solid to precipitate which was filtered off and washed thoroughly with water and diethyl ether. Recrystallisation of the solid from a chloroform/hexane mixture afforded 6.9 g 2,4-di(phenylmethyl)-6-hydroxypyrimidine as a white solid. m.pt., 158°-160° C., M+ found: 276.

후처리

  1. temperatureThe mixture was heated
  2. temperatureunder reflux
  3. temperatureby cooling
  4. customevaporation in vacuo
  5. additionWater (150 ml) was added to the residue
  6. customto precipitate which
  7. filtrationwas filtered off
  8. washwashed thoroughly with water and diethyl ether
  9. customRecrystallisation of the solid from a chloroform/hexane mixture

출처 및 근거

ORD 기록
ord-82d63ebf3c5048e2a9da1de12a330986
출처 데이터셋
uspto-grants-1994_07
특허 번호
US05332745

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