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

HRID 1463234

반응식

HRID 1463234 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-])(=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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 14798Sodium Hydroxide용매

반응 조건

온도
120 °C

실험 절차

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).

후처리

  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.

출처 및 근거

ORD 기록
ord-17711c91b7784461abcde2829759fd38
출처 데이터셋
uspto-grants-1994_04
특허 번호
US05300477

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