Methyl iodide → 3-(2-aminopyrimidin-4-yl)-5-bromo-1-methyl-2,3-dihydro-1H-1,3-benzodiazol-2-one

HRID 1398639Notes

Reaction equation

HRID 1398639 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([N:8]2[C:12]3[CH:13]=[C:14]([Br:17])[CH:15]=[CH:16][C:11]=3[NH:10][C:9]2=[O:18])[CH:5]=[CH:4][N:3]=1.[H-].[Na+].I[CH3:22]>CN(C=O)C>[NH2:1][C:2]1[N:7]=[C:6]([N:8]2[C:12]3[CH:13]=[C:14]([Br:17])[CH:15]=[CH:16][C:11]=3[N:10]([CH3:22])[C:9]2=[O:18])[CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 681820071-(2-aminopyrimidin-4-yl)-6-bromo-2,3-dihydro-1H-1,3-benzodiazol-2-one

Product 1

HCID 681816083-(2-aminopyrimidin-4-yl)-5-bromo-1-methyl-2,3-dihydro-1H-1,3-benzodiazol-2-oneYield 115%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-(2-aminopyrimidin-4-yl)-6-bromo-2,3-dihydro-1H-1,3-benzodiazol-2-one (500 mg, 1.63 mmol) in DMF (10 ml) at 0° C. was added sodium hydride (60% oil suspension, 65.33 g, 1.63 mmol). The reaction mixture was allowed to warm to RT over 5 minutes before addition of iodomethane (0.1 ml, 1.63 mmol) and stirring for 30 minutes. The mixture was quenched by addition of water (5 mL), EtOAc was then added resulting in formation of a precipitate. The precipitate was collected by suction filtration. The filtrate was extracted with EtOAc (×2). The combined organic fractions were washed with water and dried (Na2SO4), filtered and concentrated in vacuo. Combining the extract residue and the precipitate gave the crude title compound (600 mg); 1H NMR (500 MHz, CDCl3) delta 3.23 (3H, s), 5.55 (2H, s), 6.72 (1H, d, J=8.3 Hz), 7.20-7.04 (1H, m), 7.42 (1H, d, J=5.7 Hz), 8.12 (1H, d, J=5.7 Hz), 8.39 (1H, d, J=1.8 Hz); LC-MS: m/z=+321.8 (M+H)+.

Workup

  1. customThe mixture was quenched by addition of water (5 mL), EtOAc
  2. additionwas then added
  3. customresulting in formation of a precipitate
  4. filtrationThe precipitate was collected by suction filtration
  5. extractionThe filtrate was extracted with EtOAc (×2)
  6. washThe combined organic fractions were washed with water
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ea79f433d2044506b5ca791b429ac9b9
Source dataset
uspto-grants-2014_12
Patent number
US08901313B2

Reaction notes

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