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Dimethyl Sulfoxide → 9-(phenyl-amino)-6-methyl-4-oxo-6,7-dihydro-4H-pyrido[1,2-a]pyrimidine-3-carboxylic acid ethyl ester

HRID 443391
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HRID 443391 반응식
[CH2:1]([O:3][C:4]([C:6]1[C:11](=[O:12])[N:10]2[CH:13]([CH3:18])[CH2:14][CH2:15][CH:16](Br)[C:9]2=[N:8][CH:7]=1)=[O:5])[CH3:2].CS(C)=O.[NH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.O>C1C=CC=CC=1>[CH2:1]([O:3][C:4]([C:6]1[C:11](=[O:12])[N:10]2[CH:13]([CH3:18])[CH2:14][CH:15]=[C:16]([NH:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C:9]2=[N:8][CH:7]=1)=[O:5])[CH3:2]
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참가 물질

6

반응물 4

HCID 679Dimethyl SulfoxideHCID 962WaterHCID 6115AnilineHCID 134472569-bromo-6-methyl-4-oxo-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidine-3-carboxylic acid ethyl ester

생성물 1

HCID 133694119-(phenyl-amino)-6-methyl-4-oxo-6,7-dihydro-4H-pyrido[1,2-a]pyrimidine-3-carboxylic acid ethyl ester수율 59.3%

시약·촉매·용매 1

HCID 241
Benzene
용매

실험 절차

40.0 g. (0.127 mole) of 9-bromo-6-methyl-4-oxo-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidine-3-carboxylic acid ethyl ester are dissolved in 80 ml. of dimethylsulfoxide and 26 ml. (0.285 mole) of aniline are added. The solution is allowed to stand at room temperature for 3-4 days. The mixture is then diluted with 100 ml. of water, shaken out with 3×50 ml. of benzene. The combined organic layers are dried with calcinated sodium sulfate and evaporated in vacuo. The residue is recrystallized from ethanol and thus 24.5 g. (59.3%) of 9-(phenyl-amino)-6-methyl-4-oxo-6,7-dihydro-4H-pyrido[1,2-a]pyrimidine-3-carboxylic ethyl ester is obtained, melting point: 119°-120° C.

후처리

  1. additionThe mixture is then diluted with 100 ml
  2. dry with materialThe combined organic layers are dried with calcinated sodium sulfate
  3. customevaporated in vacuo
  4. customThe residue is recrystallized from ethanol and thus 24.5 g

출처 및 근거

ORD 기록
ord-306929a9f1824e4e8d397cbbfe6663e5
출처 데이터셋
uspto-grants-1981_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04260612

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