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 1163018Notes

Reaction equation

HRID 1163018 reaction equation
[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

Participants

10

Reactant 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

Product 1

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

Reagents, catalysts & solvents 5

HCID 6228DimethylformamideCatalystHCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6344DichloromethaneSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

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)

Workup

  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

Sources & evidence

ORD record
ord-7933fa9855194d3395be19fba9750855
Source dataset
uspto-grants-2010_10
Patent number
US07820818B2

Reaction notes

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