Dimethylformamide → (4-[1-[(5-Chloro-2,4-dimethoxy-phenylcarbamoyl)-methyl]-2,4-dioxo-1,4-dihydro-2H-quinazolin-3-yl}-phenyl)-acetic acid ethyl ester

HRID 472755Notes

Reaction equation

HRID 472755 reaction equation
[CH2:1]([O:3][C:4](=[O:24])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([N:12]2[C:21](=[O:22])[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[NH:14][C:13]2=[O:23])=[CH:8][CH:7]=1)[CH3:2].C([O-])([O-])=O.[K+].[K+].Br[CH2:32][C:33]([NH:35][C:36]1[CH:41]=[C:40]([Cl:42])[C:39]([O:43][CH3:44])=[CH:38][C:37]=1[O:45][CH3:46])=[O:34].CN(C=O)C>O>[CH2:1]([O:3][C:4](=[O:24])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([N:12]2[C:21](=[O:22])[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[N:14]([CH2:32][C:33](=[O:34])[NH:35][C:36]3[CH:41]=[C:40]([Cl:42])[C:39]([O:43][CH3:44])=[CH:38][C:37]=3[O:45][CH3:46])[C:13]2=[O:23])=[CH:8][CH:7]=1)[CH3:2]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 636790772-Bromo-N-(5-chloro-2,4-dimethoxy-phenyl)-acetamide2×HCID 68589607[4-(2,4-dioxo-1,4-dihydro-2H-quinazolin-3-yl)-phenyl]-acetic acid ethyl ester2×

Product 1

HCID 68591686(4-[1-[(5-Chloro-2,4-dimethoxy-phenylcarbamoyl)-methyl]-2,4-dioxo-1,4-dihydro-2H-quinazolin-3-yl}-phenyl)-acetic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A round bottomed flask charged with [4-(2,4-dioxo-1,4-dihydro-2H-quinazolin-3-yl)-phenyl]-acetic acid ethyl ester (Intermediate H) (2.0 g, 6.17 mmol), K2CO3 (2.5 eq, 2.14 g, 15.52 mmol), and 2-bromo-N-(5-chloro-2,4-dimethoxy-phenyl)-acetamide (Intermediate C) (1.02 eq, 1.99 g, 6.49 mmol) is treated with dry DMF (20 ml). The reaction is stirred at RT for 72 hours. The reaction mixture is diluted with distilled water and stirred for 15 minutes. The precipitate formed was filtered, washed with water and dried under vacuum to give the title compound; [M+H]+ 552

Workup

  1. stirringstirred for 15 minutes
  2. customThe precipitate formed
  3. filtrationwas filtered
  4. washwashed with water
  5. customdried under vacuum

Sources & evidence

ORD record
ord-3ac61f0de2454201a93cf62c879fe345
Source dataset
uspto-grants-2014_01
Patent number
US08633211B2

Reaction notes

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