Dichloromethane → (Pivaloyloxy)methyl 4-((6-(2,4-dichlorophenyl)-5-(ethoxycarbonyl)-2-(thiazol-2-yl)-3,6-dihydropyrimidin-4-yl)methyl)morpholine-3-carboxylate

HRID 524687노트

반응식

HRID 524687 반응식
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH:9]1[N:14]=[C:13]([C:15]2[S:16][CH:17]=[CH:18][N:19]=2)[NH:12][C:11]([CH2:20][N:21]2[CH2:26][CH2:25][O:24][CH2:23][CH:22]2[C:27]([OH:29])=[O:28])=[C:10]1[C:30]([O:32][CH2:33][CH3:34])=[O:31].[C:35]([O:41][CH2:42]Cl)(=[O:40])[C:36]([CH3:39])([CH3:38])[CH3:37].C(Cl)Cl>CN(C=O)C>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH:9]1[N:14]=[C:13]([C:15]2[S:16][CH:17]=[CH:18][N:19]=2)[NH:12][C:11]([CH2:20][N:21]2[CH2:26][CH2:25][O:24][CH2:23][CH:22]2[C:27]([O:29][CH2:42][O:41][C:35](=[O:40])[C:36]([CH3:39])([CH3:38])[CH3:37])=[O:28])=[C:10]1[C:30]([O:32][CH2:33][CH3:34])=[O:31]

참가 물질

5

반응물 3

HCID 6344DichloromethaneHCID 87885Chloromethyl pivalateHCID 73295969((6-(2,4-Dichlorophenyl)-5-(ethoxycarbonyl)-2-(thiazol-2-yl)-3,6-dihydropyrimidin-4-yl)methyl)morpholine-3-carboxylic acid

생성물 1

HCID 90044007(Pivaloyloxy)methyl 4-((6-(2,4-dichlorophenyl)-5-(ethoxycarbonyl)-2-(thiazol-2-yl)-3,6-dihydropyrimidin-4-yl)methyl)morpholine-3-carboxylate수율 62%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
60 °C

실험 절차

To a solution of 4-(((6-(2,4-dichlorophenyl)-5-(ethoxycarbonyl)-2-(thiazol-2-yl)-3,6-dihydropyrimidin-4-yl)methyl)morpholine-3-carboxylic acid (0.12 g, 0.23 mmol) and TEA (0.06 g, 0.6 mmol) in DMF (6 mL) was added chloromethyl pivalate (0.12 g, 0.8 mmol). And the mixture was stirred at 60° C. for 3 hours, and cooled to 25° C. To the reaction mixture was added DCM (100 mL). The organic layer was washed with brine (80 mL×6) and dried over unhydrous Na2SO4. The crude product was purified by a silica gel column chromatography (PETROLEUM ETHER/EtOAc (V/V)=8/1) to give the title compound as yellow oil (0.09 g, 62%). The compound was characterized by the following spectroscopic data:

후처리

  1. temperaturecooled to 25° C
  2. washThe organic layer was washed with brine (80 mL×6)
  3. dry with materialdried over unhydrous Na2SO4
  4. customThe crude product was purified by a silica gel column chromatography (PETROLEUM ETHER/EtOAc (V/V)=8/1)

출처 및 근거

ORD 기록
ord-c7c86253a6a54bf389bcf576c4f523b0
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09340538B2

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