Diisopropylamine → 7-Bromo-2-chloroquinazolin-8-ol

HRID 2079619Notes

Reaction equation

HRID 2079619 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.C(NC(C)C)(C)C>C(Cl)(Cl)Cl>[Br:8][C:14]1[C:13]([OH:20])=[C:12]2[C:17]([CH:18]=[N:19][C:10]([Cl:9])=[N:11]2)=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 7912DiisopropylamineHCID 67184N-bromobutanimideHCID 591992302-Chloro-8-quinazolinol

Product 1

HCID 591992277-Bromo-2-chloroquinazolin-8-olYield 51%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
-2.5 °C

Procedure

Solid NBS (1.09 g, 6.11 mmole) was added to a stirred solution of 2-chloroquinazolin-8-ol (1.10 g, 6.11 mmole) and diisopropyl amine (2.2 mL, 15.30 mmole) in CHCl3 (60 mL) at −5° C. under argon. After stirring at −5 to 0° C. for 1 hour, LCMS showed that the reaction was complete. The reaction was evaporated to a residue which was dissolved in DMSO (5 mL) and purified by prep. HPLC. The pure product was obtained as a white solid in 51% yield (800 mg, 3.08 mmole).

Workup

  1. customThe reaction was evaporated to a residue which
  2. dissolutionwas dissolved in DMSO (5 mL)
  3. custompurified by prep
  4. customThe pure product was obtained as a white solid in 51% yield (800 mg, 3.08 mmole)

Sources & evidence

ORD record
ord-e6a24652135f4e57957d9b470d18d330
Source dataset
uspto-grants-2011_04
Patent number
US07932262B2

Reaction notes

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