Methyl iodide → 8-Bromo-6-methylpyrido[4,3-d]pyrimidin-5(6H)-one

HRID 575699Notes

Reaction equation

HRID 575699 reaction equation
[H-].[Na+].[Br:3][C:4]1[C:9]2[N:10]=[CH:11][N:12]=[CH:13][C:8]=2[C:7](=[O:14])[NH:6][CH:5]=1.CI.[CH3:17]C(=O)OCC>CN(C=O)C>[Br:3][C:4]1[C:9]2[N:10]=[CH:11][N:12]=[CH:13][C:8]=2[C:7](=[O:14])[N:6]([CH3:17])[CH:5]=1

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 753583608-bromo-5H,6H-pyrido[4,3-d]pyrimidin-5-one

Product 1

HCID 1180219268-Bromo-6-methylpyrido[4,3-d]pyrimidin-5(6H)-oneYield 75.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (21 mg, 0.53 mmol, 60% in mineral oil) was added to the title compound of step 2 (100 mg, 0.44 mmol) in DMF (10 mL) at 0° C. After stirring 0.5 h, MeI (126 mg, 0.88 mmol) was added and stirring continued at 0° C. for 2 h. Following extractive work up with EA, the title compound (80 mg, yield: 75.3%) was obtained as a yellow solid. 1H NMR: (DMSO-d6, 400 MHz) δ: 9.47 (s, 1H), 9.46 (s, 1H), 8.53 (s, 1H), 3.54 (s, 3H). LCMS: 240.0, 242.0 (M+H)+.

Workup

  1. stirringstirring
  2. waitcontinued at 0° C. for 2 h

Sources & evidence

ORD record
ord-6b64b1f96bce45eeb3e16860b7223398
Source dataset
uspto-grants-2015_05
Patent number
US09034900B2

Reaction notes

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