Methyl iodide → HCID 66609624, compound

HRID 473144Notes

Reaction equation

HRID 473144 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([SH:22])=[N:7][C:8]([C:12]([F:21])([F:20])[C:13]3[CH:18]=[CH:17][C:16]([F:19])=[CH:15][N:14]=3)=[N:9]2)=[CH:4][CH:3]=1.[OH-].[Na+].I[CH3:26]>C(O)(C)C>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([S:22][CH3:26])=[N:7][C:8]([C:12]([F:20])([F:21])[C:13]3[CH:18]=[CH:17][C:16]([F:19])=[CH:15][N:14]=3)=[N:9]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 14798Sodium HydroxideHCID 178505733HCID 178505733, compound

Product 1

HCID 66609624HCID 66609624, compoundYield 72.2%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To 7-bromo-2-(difluoro(5-fluoropyridin-2-yl)methyl)quinazoline-4-thiol (500 mg, 1.29 mmol) in isopropanol (10 mL) were added 1N NaOH (1.94 mL, 1.94 mmol) and iodomethane (0.097 mL, 1.55 mmol) and the mixture was stirred at rt for 30 min. A brown solid formed, which was collected by filtration and washed with MeOH to afford 7-bromo-2-(difluoro(5-fluoropyridin-2-yl)methyl)-4-(methylthio)quinazoline (0.373 g, 72%). 1H NMR (300 MHz, CDCl3) δ 8.45-8.51 (m, 1H), 8.26-8.32 (m, 1H), 7.93-8.03 (m, 2H), 7.74 (dd, J=1.9, 8.9 Hz, 1H), 7.54-7.65 (m, 1H), 2.61 (s, 3H); LC-MS (ESI) m/z 400/402 (M+H)+.

Workup

  1. customA brown solid formed
  2. filtrationwhich was collected by filtration
  3. washwashed with MeOH

Sources & evidence

ORD record
ord-f699aec0685846a3a044a778a47c7ad9
Source dataset
uspto-grants-2014_01
Patent number
US08633207B2

Reaction notes

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