Potassium Carbonate → {1-[(5-chloro-2,4-dimethoxy-phenylcarbamoyl)-methyl]-2,4-dioxo-1,4-dihydro-2H-quinazolin-3-yl}-acetic acid methyl ester

HRID 472743Notes

Reaction equation

HRID 472743 reaction equation
[CH3:1][O:2][C:3](=[O:17])[CH2:4][N:5]1[C:14](=[O:15])[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[NH:7][C:6]1=[O:16].C([O-])([O-])=O.[K+].[K+].Br[CH2:25][C:26]([NH:28][C:29]1[CH:34]=[C:33]([Cl:35])[C:32]([O:36][CH3:37])=[CH:31][C:30]=1[O:38][CH3:39])=[O:27]>CN(C=O)C.O>[CH3:1][O:2][C:3](=[O:17])[CH2:4][N:5]1[C:14](=[O:15])[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[N:7]([CH2:25][C:26](=[O:27])[NH:28][C:29]2[CH:34]=[C:33]([Cl:35])[C:32]([O:36][CH3:37])=[CH:31][C:30]=2[O:38][CH3:39])[C:6]1=[O:16]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 906854methyl (2,4-dioxo-1,4-dihydroquinazolin-3(2H)-yl)acetateHCID 636790772-Bromo-N-(5-chloro-2,4-dimethoxy-phenyl)-acetamide2×

Product 1

HCID 68588223{1-[(5-chloro-2,4-dimethoxy-phenylcarbamoyl)-methyl]-2,4-dioxo-1,4-dihydro-2H-quinazolin-3-yl}-acetic acid methyl ester

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of (2,4-dioxo-1,4-dihydro-2H-quinazolin-3-yl)-acetic acid methyl ester (1 g, 4.27 mmol), K2CO3 (910 mg, 6.404 mmol) and 2-bromo-N-(5-chloro-2,4-dimethoxy-phenyl)-acetamide (Intermediate C) (1.42 g, 4.697 mmol) in dry DMF (6 ml) is left to stir at RT overnight. The reaction mixture is diluted with water resulting in a cream precipitate which is filtered, washed with water and dried under vacuum to give the title compound as a pale yellow solid [M+H]+ 462.

Workup

  1. waitis left
  2. filtrationis filtered
  3. washwashed with water
  4. customdried under vacuum

Sources & evidence

ORD record
ord-8612ff16acd549b09ab54092d2177f51
Source dataset
uspto-grants-2014_01
Patent number
US08633211B2

Reaction notes

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