1,8-Diazabicyclo(5.4.0)undec-7-ene → 5-Chloro-N-((1-(4-(2-oxopyrimidin-1(2H)-yl)phenyl)-1H-1,2,3-triazol-4-yl)methyl)thiophene-2-carboxamide

HRID 642981Notes

Reaction equation

HRID 642981 reaction equation
[N:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH:15]=[CH:14][CH:13]=[N:12][C:11]2=[O:16])=[CH:6][CH:5]=1)=[N+:2]=[N-:3].[Cl:17][C:18]1[S:22][C:21]([C:23]([NH:25][CH2:26][C:27]#[CH:28])=[O:24])=[CH:20][CH:19]=1.C1CCN2C(=NCCC2)CC1>CO.C(#N)C.[Cu]I>[Cl:17][C:18]1[S:22][C:21]([C:23]([NH:25][CH2:26][C:27]2[N:3]=[N:2][N:1]([C:4]3[CH:9]=[CH:8][C:7]([N:10]4[CH:15]=[CH:14][CH:13]=[N:12][C:11]4=[O:16])=[CH:6][CH:5]=3)[CH:28]=2)=[O:24])=[CH:20][CH:19]=1

Participants

7

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 38511805-chloro-N-(prop-2-yn-1-yl)thiophene-2-carboxamide2×HCID 592600781-(4-azidophenyl)pyrimidin-2(1H)-one

Product 1

HCID 249909425-Chloro-N-((1-(4-(2-oxopyrimidin-1(2H)-yl)phenyl)-1H-1,2,3-triazol-4-yl)methyl)thiophene-2-carboxamide

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 887MethanolSolventHCID 6342AcetonitrileSolvent

Procedure

1-(4-Azidophenyl)pyrimidin-2(1H)-one (2.4, 20 mg, 0.09 mmol) was dissolved in 5 mL methanol. To it were added 5-chloro-N-(prop-2-ynyl)thiophene-2-carboxamide (compound 1.4, 18 mg, 0.09 mmol), DBU (26 μL, 0.18 mmol) and CuI (17 mg, 0.09 mmol). The mixture was stirred for 2 hrs at RT, diluted with 30 mL acetonitrile, filtered through celite, concentrated in vacuo and subjected to prep HPLC to isolate the title compound. MS found for C18H13ClN6O2S (M+H)+ 413.0, 415.0 (Cl pattern).

Workup

  1. filtrationfiltered through celite
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9203fe5a86314ba0ad197936a84a75a3
Source dataset
uspto-grants-2010_04
Patent number
US07696352B2

Reaction notes

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