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

HRID 645520ノート

反応式

HRID 645520 の反応式
[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

参加物

7

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-3db8fb840033460fa295ad251a5fb9de
出典データセット
uspto-grants-2010_04
特許番号
US07704996B2

反応ノート

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