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 1163018노트

반응식

HRID 1163018 반응식
[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

참가 물질

10

반응물 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

생성물 1

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

시약·촉매·용매 5

HCID 6228Dimethylformamide촉매HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 6344Dichloromethane용매HCID 8058Hexane용매HCID 8857Ethyl Acetate용매

실험 절차

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 CH2Cl2 (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)

후처리

  1. customevaporated
  2. dissolutionThe residue is dissolved in CH2Cl2 (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

출처 및 근거

ORD 기록
ord-7933fa9855194d3395be19fba9750855
출처 데이터셋
uspto-grants-2010_10
특허 번호
US07820818B2

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