N-bromobutanimide → 5-Bromo-2-chloroquinazolin-8-ol

HRID 2079673Notes

Reaction equation

HRID 2079673 reaction equation
C1C(=O)N([Br:8])C(=O)C1.[Cl:9][C:10]1[N:19]=[CH:18][C:17]2[C:12](=[C:13]([OH:20])[CH:14]=[CH:15][CH:16]=2)[N:11]=1>CN1C(=O)CCC1.C(OCC)(=O)C>[Br:8][C:16]1[CH:15]=[CH:14][C:13]([OH:20])=[C:12]2[C:17]=1[CH:18]=[N:19][C:10]([Cl:9])=[N:11]2

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 591992302-Chloro-8-quinazolinol

Product 1

HCID 866393225-Bromo-2-chloroquinazolin-8-olYield 60%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
0 °C

Procedure

Solid NBS (1 eq) was added to a stirred solution of 2-chloroquinazolin-8-ol (1 eq) (See example 1 for synthesis) in NMP at 0° C. under argon. After stirring at 0° C. for 30 min, LCMS showed that the reaction was complete. The formation of both 5-bromo (Major) and 7-bromo (Minor) isomers along with 5,7 dibromo product was observed. The reaction mixture was diluted with ethyl acetate and washed with satd. sodium bicarbonate, water and brine. Dried, filtered and concentrated. The crude was purified by flash chromatography (3-5% EtOAc/Hexane) to provide 5-bromo-2-chloroquinazolin-8-ol as a white solid in 60% yield. ES/MS m/z 259.2 (MH+).

Workup

  1. washwashed with satd
  2. customDried
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude was purified by flash chromatography (3-5% EtOAc/Hexane)

Sources & evidence

ORD record
ord-d6c65847e82f43298e76053d7a414829
Source dataset
uspto-grants-2011_04
Patent number
US07932262B2

Reaction notes

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