Methanol → HCID 71743939, compound

HRID 2280997Notes

Reaction equation

HRID 2280997 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][C:9]([CH:12](Br)Br)=[C:8]2[C:3]=1[CH:4]=[N:5][CH:6]=[N:7]2.C(O)(C(F)(F)F)=[O:16].CO.[NH4+].[OH-]>CC(C)=O.O.[N+]([O-])([O-])=O.[Ag+]>[Br:1][C:2]1[CH:11]=[CH:10][C:9]([CH:12]=[O:16])=[C:8]2[C:3]=1[CH:4]=[N:5][CH:6]=[N:7]2

Participants

8

Reactant 4

HCID 887MethanolHCID 6422Trifluoroacetic acidHCID 14923Ammonium HydroxideHCID 896475325-Bromo-8-(dibromomethyl)quinazoline

Product 1

HCID 71743939HCID 71743939, compound

Reagents, catalysts & solvents 3

HCID 24470Silver NitrateCatalystHCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

To a stirred solution of 5-Bromo-8-(dibromomethyl) quinazoline (61 g, crude mixture) in Acetone (500 mL) and water (100 mL), was added silver nitrate (61 g) in portions at 0° C. The reaction mixture was stirred at RT for 6 h. The reaction completion was confirmed by TLC. The reaction mixture was filtered off and filtrate was extracted with ethyl acetate (3×500 mL). The organic layer was washed with 10% NaHCO3 solution, water and brine solution. The solvent was dried over Na2SO4 and concentrated under vacuum to afford the crude product with HPLC (56%) (25 g, 65%) was subjected to prep.HPLC condition: COLUMN: Xterra, C18 (19×300 mm), 10 micron, Mobile: 0.1% TFA; B: MeOH to isolate the compound. The resulted solid was basified with NH4OH and extracted with EtOAc. The organic layer was washed water. The solvent was dried over Na2SO4 and concentrated under vacuum to yield (6.2 g) of the titled compound as pale yellow solid. 1H NMR (DMSO-d6, 400 MHz) 11.14 (s, 1H), 9.80 (s, 1H), 9.58 (s, 1H), 8.30-8.27 (d, J=12.3 Hz, 2H).

Workup

  1. filtrationThe reaction mixture was filtered off
  2. extractionfiltrate was extracted with ethyl acetate (3×500 mL)
  3. washThe organic layer was washed with 10% NaHCO3 solution, water and brine solution
  4. dry with materialThe solvent was dried over Na2SO4
  5. concentrationconcentrated under vacuum
  6. customto afford the crude product with HPLC (56%) (25 g, 65%)
  7. extractionextracted with EtOAc
  8. washThe organic layer was washed water
  9. dry with materialThe solvent was dried over Na2SO4
  10. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-52bff7e8c83a485db246bbc4e0b388dd
Source dataset
uspto-grants-2015_09
Patent number
US09139568B2

Reaction notes

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