Triethylamine → 2-(2-Acetylaminopyrimidin-4-ylmethylthio)-N-(3,5-dimethylphenyl)pyridine-3-carboxamide

HRID 602308Notes

Reaction equation

HRID 602308 reaction equation
C(N(CC)CC)C.[CH3:8][C:9]1[CH:10]=[C:11]([NH:16][C:17]([C:19]2[C:20](=[S:25])[NH:21][CH:22]=[CH:23][CH:24]=2)=[O:18])[CH:12]=[C:13]([CH3:15])[CH:14]=1.[C:26]([NH:29][C:30]1[N:35]=[C:34]([CH2:36]Cl)[CH:33]=[CH:32][N:31]=1)(=[O:28])[CH3:27].C(OCC)(=O)C>CN(C)C=O>[C:26]([NH:29][C:30]1[N:35]=[C:34]([CH2:36][S:25][C:20]2[C:19]([C:17]([NH:16][C:11]3[CH:12]=[C:13]([CH3:15])[CH:14]=[C:9]([CH3:8])[CH:10]=3)=[O:18])=[CH:24][CH:23]=[CH:22][N:21]=2)[CH:33]=[CH:32][N:31]=1)(=[O:28])[CH3:27]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 23151038N-(3,5-Dimethylphenyl)-2-thioxo-1,2-dihydropyridine-3-carboxamideHCID 451192602-Acetylamino-4-chloromethylpyrimidine

Product 1

HCID 119648552-(2-Acetylaminopyrimidin-4-ylmethylthio)-N-(3,5-dimethylphenyl)pyridine-3-carboxamideYield 52%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Triethylamine (45 μL, 0.32 mmol) was added to a solution of N-(3,5-dimethylphenyl)-2-thioxo-1,2-dihydropyridine-3-carboxamide (28 mg, 0.11 mmol, Reference Compound No. 13-1) and 2-acetylamino-4-(chloromethyl)pyrimidine (18 mg, 0.10 mmol, Reference Compound No. 11-1) in anhydrous N,N-dimethylformamide (1.0 mL) at room temperature, and the mixture was stirred for 16 hours. Ethyl acetate (30 mL) was added thereto, then the whole was washed with saturated aqueous sodium hydrogen carbonate solution (30 mL) and brine (30 mL), and the organic layer was dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and then the precipitated solid was filtered off with diethyl ether and washed. The solid was dried at 50° C. under reduced pressure to give 21 mg of the target compound as a light orange solid (Yield: 52%).

Workup

  1. washthe whole was washed with saturated aqueous sodium hydrogen carbonate solution (30 mL) and brine (30 mL)
  2. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  3. customThe solvent was evaporated under reduced pressure
  4. filtrationthe precipitated solid was filtered off with diethyl ether
  5. washwashed
  6. customThe solid was dried at 50° C. under reduced pressure

Sources & evidence

ORD record
ord-ac146673aa2947188d00dae1017566d2
Source dataset
uspto-grants-2011_03
Patent number
US07906511B2

Reaction notes

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