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Dichloromethane → 4-chloro-5-[N-(2-pyrimidinylmethyl)carbamoyl]-6-methoxy-2-methylthiopyrimidine

HRID 917656
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HRID 917656 반응식
[Cl:1][C:2]1[C:7]([C:8](Cl)=[O:9])=[C:6]([O:11][CH3:12])[N:5]=[C:4]([S:13][CH3:14])[N:3]=1.C(Cl)Cl.[NH2:18][CH2:19][C:20]1[N:25]=[CH:24][CH:23]=[CH:22][N:21]=1.C(N(CC)CC)C>O>[Cl:1][C:2]1[C:7]([C:8](=[O:9])[NH:18][CH2:19][C:20]2[N:25]=[CH:24][CH:23]=[CH:22][N:21]=2)=[C:6]([O:11][CH3:12])[N:5]=[C:4]([S:13][CH3:14])[N:3]=1
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참가 물질

6

반응물 4

HCID 6344Dichloromethane2회HCID 8471TriethylamineHCID 46580472-PyrimidinemethanamineHCID 178482844-Chloro-5-chloroformyl-6-methoxy-2-methylthiopyrimidine

생성물 1

HCID 211000644-chloro-5-[N-(2-pyrimidinylmethyl)carbamoyl]-6-methoxy-2-methylthiopyrimidine

시약·촉매·용매 1

HCID 962
Water
용매

실험 절차

To a mixture of whole amount of 4-chloro-5-chloroformyl-6-methoxy-2-methylthiopyrimidine (prepared in the above (4)) and methylene chloride 10 ml is dropped a mixture of 2-aminomethylpyrimidine 930 mg, triethylamine 2.38 ml and methylene chloride 10 ml over a period of 5 minutes on an ice bath, and the mixture is stirred for 20 minutes. The mixture is further stirred at room temperature for 40 minutes. The reaction mixture is diluted with water and the water layer is extracted with methylene chloride. The organic layer is dried and concentrated in vacuo. The residue is separated with silica gel chromatography (solvent; chloroform:ethyl acetate=1:1) and recrystallized from a mixture of methylene chloride, ethyl acetate and isopropyl ether to give 4-chloro-5-[N-(2-pyrimidinylmethyl)carbamoyl]-6-methoxy-2-methylthiopyrimidine as a colorless crystalline powder, 1.56 g. mp 176-177° C.

후처리

  1. additionis dropped
  2. stirringThe mixture is further stirred at room temperature for 40 minutes
  3. extractionthe water layer is extracted with methylene chloride
  4. customThe organic layer is dried
  5. concentrationconcentrated in vacuo
  6. customThe residue is separated with silica gel chromatography (solvent; chloroform:ethyl acetate=1:1)
  7. customrecrystallized from a mixture of methylene chloride, ethyl acetate and isopropyl ether

출처 및 근거

ORD 기록
ord-48609a4ab1fd45e9a89531e9764cbafa
출처 데이터셋
uspto-grants-2007_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07273868B2

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