Methyl iodide → 6-[(1-Bromoimidazo[1,5-a]pyridin-3-yl)carbonyl]-3-(4-fluorobenzyl)-1-methylquinazoline-2,4(1H,3H)-dione

HRID 409547Notes

Reaction equation

HRID 409547 reaction equation
[C:1](=O)([O-])[O-].[Cs+].[Cs+].CI.[Br:9][C:10]1[N:11]=[C:12]([C:19]([C:21]2[CH:22]=[C:23]3[C:28](=[CH:29][CH:30]=2)[NH:27][C:26](=[O:31])[N:25]([CH2:32][C:33]2[CH:38]=[CH:37][C:36]([F:39])=[CH:35][CH:34]=2)[C:24]3=[O:40])=[O:20])[N:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=12>CN(C=O)C>[Br:9][C:10]1[N:11]=[C:12]([C:19]([C:21]2[CH:22]=[C:23]3[C:28](=[CH:29][CH:30]=2)[N:27]([CH3:1])[C:26](=[O:31])[N:25]([CH2:32][C:33]2[CH:34]=[CH:35][C:36]([F:39])=[CH:37][CH:38]=2)[C:24]3=[O:40])=[O:20])[N:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=12

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 866834556-[(1-bromoimidazo[1,5-a]pyridin-3-yl)carbonyl]-3-(4-fluorobenzyl)quinazoline-2,4(1H,3H)-dione

Product 1

HCID 866834546-[(1-Bromoimidazo[1,5-a]pyridin-3-yl)carbonyl]-3-(4-fluorobenzyl)-1-methylquinazoline-2,4(1H,3H)-dioneYield 96.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.87 g (5.7 mmol) of caesium carbonate and 0.39 ml (6.2 mmol) of methyl iodide are added, at ambient temperature under an inert atmosphere, to 2.6 g (5.17 mmol) of 6-[(1-bromoimidazo[1,5-a]pyridin-3-yl)carbonyl]-3-(4-fluorobenzyl)quinazoline-2,4(1H,3H)-dione in 50 ml of anhydrous DMF. The reaction medium is stirred for 18 hours at ambient temperature and then filtered. The precipitate is rinsed with water and then dried under reduced pressure at 50° C. overnight. 2.54 g of a yellow solid are obtained.

Workup

  1. filtrationfiltered
  2. washThe precipitate is rinsed with water
  3. customdried under reduced pressure at 50° C. overnight

Sources & evidence

ORD record
ord-4a9cd953042744f596e17b8e2b6dcabc
Source dataset
uspto-grants-2014_06
Patent number
US08759344B2

Reaction notes

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