Methanol → 7,8-dimethoxy-4-(3-bromo-phenyl)-5,6-dihydro-4H-1,3,4-triaza-phenalen-5-ol

HRID 1351224Notes

Reaction equation

HRID 1351224 reaction equation
[CH2:1]([C:4]1[C:13]([O:14][CH3:15])=[C:12]([O:16][CH3:17])[CH:11]=[C:10]2[C:5]=1[C:6]([NH:18][C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([Br:25])[CH:20]=1)=[N:7][CH:8]=[N:9]2)[CH:2]=C.C[OH:27]>>[CH3:15][O:14][C:13]1[C:12]([O:16][CH3:17])=[CH:11][C:10]2=[C:5]3[C:4]=1[CH2:1][CH:2]([OH:27])[N:18]([C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([Br:25])[CH:20]=1)[C:6]3=[N:7][CH:8]=[N:9]2

Participants

3

Reactant 2

HCID 887MethanolHCID 11177044(5-Allyl-6,7-dimethoxy-quinazolin-4-yl)-(3-bromo-phenyl)-amine

Product 1

HCID 112466327,8-dimethoxy-4-(3-bromo-phenyl)-5,6-dihydro-4H-1,3,4-triaza-phenalen-5-ol

Procedure

To a solution of (5-allyl-6,7-dimethoxy-quinazolin-4-yl)-(3-bromo-phenyl)-amine (0.17 g, 0.42 mmol) (from Example 17, Step E, supra) in methanol (50 mL) at −78° C. was passed a continuous stream of 03 until the color of the solution became blue. The reaction solution was then purged with argon, and methyl sulfide (5 mL) (Aldrich) was added. The reaction mixture was slowly warmed to room temperature and stirred overnight. The solution was concentrated, the residue was dried in vacuo to give the desired 7,8-dimethoxy-4-(3-bromo-phenyl)-5,6-dihydro-4H-1,3,4-triaza-phenalen-5-ol as a crude brown oil. (Yield 0.16g, 100%).

Workup

  1. customat −78° C.
  2. customThe reaction solution was then purged with argon, and methyl sulfide (5 mL) (Aldrich)
  3. additionwas added
  4. concentrationThe solution was concentrated
  5. customthe residue was dried in vacuo

Sources & evidence

ORD record
ord-4810135bdbdf4c20b02e109c37e338ba
Source dataset
uspto-grants-2007_05
Patent number
US07217717B2

Reaction notes

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