Triethylamine → 4-(2,2-Dimethyl-propylamino)-5-[3-oxo-3-(4-[1,2,3]triazol-1-yl-phenyl)-prop-1-ynyl]-pyrimidine-2-carbonitrile

HRID 1984243ノート

反応式

HRID 1984243 の反応式
[N:1]1([C:6]2[CH:14]=[CH:13][C:9]([C:10]([OH:12])=O)=[CH:8][CH:7]=2)[CH:5]=[CH:4][N:3]=[N:2]1.C(Cl)(=O)C(Cl)=O.[CH3:21][C:22]([CH3:36])([CH3:35])[CH2:23][NH:24][C:25]1[C:30]([C:31]#[CH:32])=[CH:29][N:28]=[C:27]([C:33]#[N:34])[N:26]=1.C(N(CC)CC)C>C(Cl)Cl.CN(C=O)C.[Cu]I.CCOC(C)=O.CCCCCC>[CH3:21][C:22]([CH3:36])([CH3:35])[CH2:23][NH:24][C:25]1[C:30]([C:31]#[C:32][C:10](=[O:12])[C:9]2[CH:8]=[CH:7][C:6]([N:1]3[CH:5]=[CH:4][N:3]=[N:2]3)=[CH:14][CH:13]=2)=[CH:29][N:28]=[C:27]([C:33]#[N:34])[N:26]=1

参加物

10

反応物 4

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 226280454-(1H-1,2,3-triazol-1-yl)benzoic acidHCID 577141354-(2,2-Dimethyl-propylamino)-5-ethynyl-pyrimidine-2-carbonitrile

生成物 1

HCID 577141314-(2,2-Dimethyl-propylamino)-5-[3-oxo-3-(4-[1,2,3]triazol-1-yl-phenyl)-prop-1-ynyl]-pyrimidine-2-carbonitrile収率 31%

試薬・触媒・溶媒 5

HCID 6228Dimethylformamide触媒HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 6344Dichloromethane溶媒HCID 8058Hexane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

4-[1,2,3]Triazol-1-yl-benzoic acid (5.0 mmol) is dissolved in CH2Cl2 (20 ml). Oxalyl chloride (3.5 mmol) and DMF (1 drop) are added at room temperature and the reaction mixture is stirred at room temperature for 3 h, then evaporated. The residue is dissolved in CH2C2 (20 ml) and the mixture is added to 4-(2,2-dimethyl-propylamino)-5-ethynyl-pyrimidine-2-carbonitrile, copper (I) iodide (0.13 mmol) and triethylamine (13.0 mmol) at room temperature. The reaction mixture is stirred for overnight at room temperature. The organic layer is washed with brine, dried over magnesium sulfate and concentrated. The crude product is purified by silica gel column chromatography to give the product in 31% yield. Rf=0.02 (n-hexane:AcOEt=2:1)

後処理

  1. customevaporated
  2. dissolutionThe residue is dissolved in CH2C2 (20 ml)
  3. stirringThe reaction mixture is stirred for overnight at room temperature
  4. washThe organic layer is washed with brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated
  7. customThe crude product is purified by silica gel column chromatography
  8. customto give the product in 31% yield

出典と根拠

ORDレコード
ord-60f639cdeaae4888a3bb5ee33124be62
出典データセット
uspto-grants-2009_06
特許番号
US07544688B2

反応ノート

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