Methyl iodide → 5-(3-bromo-phenyl)-3-methyl-2-methylsulfanyl-6-pyridin-4-yl-3H-pyrimidin-4-one

HRID 1795448Notes

Reaction equation

HRID 1795448 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([O:11]CC)=O)[CH:5]=[CH:6][CH:7]=1.[C:14]([C:16]1[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=1)#[N:15].CC([O-])(C)C.[K+].[CH3:28][N:29]=[C:30]=[S:31].I[CH3:33]>CC(O)(C)C.CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]([C:8]2[C:9](=[O:11])[N:29]([CH3:28])[C:30]([S:31][CH3:33])=[N:15][C:14]=2[C:16]2[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=2)[CH:5]=[CH:6][CH:7]=1

Participants

8

Reactant 5

HCID 6328Methyl iodideHCID 75064-CyanopyridineHCID 11167Methyl isothiocyanateHCID 11470552Ethyl 3-(bromophenyl)acetateHCID 23665647Potassium tert-butoxide

Product 1

HCID 221852215-(3-bromo-phenyl)-3-methyl-2-methylsulfanyl-6-pyridin-4-yl-3H-pyrimidin-4-one

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6386tert-ButanolSolvent

Procedure

To a 500 mL round bottom flask (RBF), was added ethyl (3-bromo-phenyl)acetate (10.3 g, 42.2 mmol), 4-cyanopyridine (4.4 g, 42.2 mmol) and 56 mL DMF. The mixture was stirred at room temperature under nitrogen. 42 mL 1 M KOtBu in tBuOH was added drop wise, and stirred for 1 h at rt. Methyl isothiocyanate (3.08 g, 42.2 mmol) was added in one portion, and stirred for another one hour at rt. The mixture was cooled down to 0° C., iodomethane (2.7 mL, 42.2 mmol) was added drop wise and stirred for 1 h at 0° C. To quench the reaction, 100 mL H2O was added. Yellow solid was precipitated. After filtration and washed with H2O, the 5-(3-bromo-phenyl)-3-methyl-2-methylsulfanyl-6-pyridin-4-yl-3H-pyrimidin-4-one was obtained in 9.2 g as pale yellow powder. MS (ES+): 388 (M+H)+; (ES−): 386 (M−H).

Workup

  1. stirringstirred for 1 h at rt
  2. stirringstirred for another one hour at rt
  3. temperatureThe mixture was cooled down to 0° C.
  4. stirringstirred for 1 h at 0° C
  5. customTo quench
  6. customthe reaction, 100 mL H2O
  7. additionwas added
  8. customYellow solid was precipitated
  9. filtrationAfter filtration
  10. washwashed with H2O

Sources & evidence

ORD record
ord-9a3944b82f2b4a45a2b8c67ea474ba44
Source dataset
uspto-grants-2006_04
Patent number
US07026326B2

Reaction notes

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