Ethyl bromoacetate → Ethyl {3-[(4-bromo-2-fluorophenyl)methyl]-7-chloro-2,4-dioxo-3,4-dihydroquinazolin-1(2H)-yl}acetate

HRID 1639312Notes

Reaction equation

HRID 1639312 reaction equation
[Br:1][C:2]1[CH:21]=[CH:20][C:5]([CH2:6][N:7]2[C:16](=[O:17])[C:15]3[C:10](=[CH:11][C:12]([Cl:18])=[CH:13][CH:14]=3)[NH:9][C:8]2=[O:19])=[C:4]([F:22])[CH:3]=1.Br[CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Br:1][C:2]1[CH:21]=[CH:20][C:5]([CH2:6][N:7]2[C:16](=[O:17])[C:15]3[C:10](=[CH:11][C:12]([Cl:18])=[CH:13][CH:14]=3)[N:9]([CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])[C:8]2=[O:19])=[C:4]([F:22])[CH:3]=1

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 144237993-(4-bromo-2-fluorobenzyl)-7-chloro-2,4(1H,3H)-quinazolinedione

Product 1

HCID 11431340Ethyl {3-[(4-bromo-2-fluorophenyl)methyl]-7-chloro-2,4-dioxo-3,4-dihydroquinazolin-1(2H)-yl}acetateYield 89.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 3-(4-bromo-2-fluorobenzyl)-7-chloro-1,2,3,4-tetrahydro-2,4-dioxoquinazoline (500 mg), ethyl bromoacetate (218 mg) and potassium carbonate (360 mg) in N,N-dimethylformamide (5 ml) was stirred at 30° C. for 30 minutes. The solution was evaporated and the residue was dissolved in ethyl acetate. The solution was washed in turn with 0.5N aqueous hydrochloric acid and water, and then dried over magnesium sulfate. The solvent was removed in vacuo to give a crystalline residue, which was crystallized from a mixture of ethyl acetate and n-hexane to give ethyl 2-[3-(4-bromo-2-fluorobenzyl)-7-chloro-1,2,3,4-tetrahydro-2,4-dioxoquinazolin-1-yl]acetate (550 mg).

Workup

  1. customThe solution was evaporated
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washThe solution was washed in turn with 0.5N aqueous hydrochloric acid and water
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was removed in vacuo
  6. customto give a crystalline residue, which
  7. customwas crystallized from a mixture of ethyl acetate and n-hexane

Sources & evidence

ORD record
ord-da1caf00f70f43c8b47dc88d6a12ba1e
Source dataset
uspto-grants-1989_11
Patent number
US04883800

Reaction notes

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