Benzylamine → N-benzyl-4,6-dichloro-2-(methylthio)pyrimidine-5-carboxamide

HRID 645520노트

반응식

HRID 645520 반응식
[Cl:1][C:2]1[C:7]([C:8](Cl)=[O:9])=[C:6]([Cl:11])[N:5]=[C:4]([S:12][CH3:13])[N:3]=1.C(N(CC)CC)C.[CH2:21]([NH2:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C1COCC1.CCOC(C)=O.O>[CH2:21]([NH:28][C:8]([C:7]1[C:6]([Cl:11])=[N:5][C:4]([S:12][CH3:13])=[N:3][C:2]=1[Cl:1])=[O:9])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

참가 물질

7

반응물 3

HCID 7504BenzylamineHCID 8471TriethylamineHCID 726991444,6-Dichloro-2-(methylthio)pyrimidine-5-carbonyl chloride

생성물 1

HCID 86627801N-benzyl-4,6-dichloro-2-(methylthio)pyrimidine-5-carboxamide

시약·촉매·용매 3

HCID 962Water용매HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of 4,6-dichloro-2-methylsulfanylpyrimidine-5-carbonyl chloride in THF (15 mL), triethylamine (2.3 mmol) and benzylamine (2.5 mmol) are added at 0° C. After stirred at room temperature for 2 h, the reaction mixture is diluted with AcOEt and H2O. The mixture is extracted twice with AcOEt. The organic layer is dried over Na2SO4, filtered, and concentrated. The residue is purified by silica gel column chromatography to give 4,6-dichloro-2-methylsulfanylpyrimidine-5-carboxylic acid benzylamide as a white solid. 1H-NMR (CDCl3), δ 2.57 (3H, s), 4.66 (2H, d), 6.08 (1H, br s), 7.31-7.35 (2H, m), 7.36-7.38 (3H, m).

후처리

  1. extractionThe mixture is extracted twice with AcOEt
  2. dry with materialThe organic layer is dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue is purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-3db8fb840033460fa295ad251a5fb9de
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07704996B2

반응 노트

불러오는 중…