Piconol → 2-Methylthio-4-(3-chloro-4-methoxybenzylamino)-5-(2-pyridylmethoxycarbonyl)pyrimidine

HRID 917592노트

반응식

HRID 917592 반응식
[CH3:1][S:2][C:3]1[N:8]=[C:7]([NH:9][CH2:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[C:13]([Cl:19])[CH:12]=2)[C:6]([C:20]([OH:22])=[O:21])=[CH:5][N:4]=1.ClC1C=C(Cl)C=C(Cl)C=1C(Cl)=O.CN(C1C=CC=CN=1)C.[N:44]1[CH:49]=[CH:48][CH:47]=[CH:46][C:45]=1[CH2:50]O>O1CCCC1.O.C(OCC)(=O)C.C(N(CC)CC)C>[CH3:1][S:2][C:3]1[N:8]=[C:7]([NH:9][CH2:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[C:13]([Cl:19])[CH:12]=2)[C:6]([C:20]([O:22][CH2:50][C:45]2[CH:46]=[CH:47][CH:48]=[CH:49][N:44]=2)=[O:21])=[CH:5][N:4]=1

참가 물질

9

반응물 4

HCID 11474PiconolHCID 218852-DimethylaminopyridineHCID 27337032,4,6-Trichlorobenzoyl chlorideHCID 226655724-((3-Chloro-4-methoxybenzyl)amino)-2-(methylthio)pyrimidine-5-carboxylic acid

생성물 1

HCID 178483432-Methylthio-4-(3-chloro-4-methoxybenzylamino)-5-(2-pyridylmethoxycarbonyl)pyrimidine

시약·촉매·용매 4

HCID 962Water용매HCID 8028Tetrahydrofuran용매HCID 8471Triethylamine용매HCID 8857Ethyl Acetate용매

실험 절차

A mixture of 2-methylthio-4-(3-chloro-4-methoxybenzylamino)-5-carboxypyrimidine (prepared in Example 79) 0.100 g and triethylamine 82 μl in tetrahydrofuran 2.0 ml is treated under room temperature with 2,4,6-trichlorobenzoyl chloride 51 μl and then dimethylaminopyridine about 1 mg is added thereto, followed by stirring for 10 minutes. After addition of 2-pyridinemethanol 31 μl, the mixture is stirred for 12 hours. Ethyl acetate and water are added thereto and the organic layer is separated, washed with sodium hydrogen carbonate solution, brine. The organic layer is dried over anhydrous sodium sulfate and in vacuo. The residue is purified with silica gel chromatography (solvent; chloroform:ethyl acetate=5:1-2:1) and recrystallized from ethyl acetate-isopropyl ether to give 2-methylthio-4-(3-chloro-4-methoxybenzylamino)-5-(2-pyridylmethoxycarbonyl)pyrimidine as a colorless needle, 0.5183 g. mp 117-118° C.

후처리

  1. stirringthe mixture is stirred for 12 hours
  2. customthe organic layer is separated
  3. washwashed with sodium hydrogen carbonate solution, brine
  4. dry with materialThe organic layer is dried over anhydrous sodium sulfate and in vacuo
  5. customThe residue is purified with silica gel chromatography (solvent; chloroform:ethyl acetate=5:1-2:1)
  6. customrecrystallized from ethyl acetate-isopropyl ether

출처 및 근거

ORD 기록
ord-47a282a30901414e910330766c98f36f
출처 데이터셋
uspto-grants-2007_09
특허 번호
US07273868B2

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