Formamide → 6,7-Dimethoxy-4-methylquinazoline

HRID 2063292Notes

Reaction equation

HRID 2063292 reaction equation
[CH3:1][C:2]([C:4]1[C:9]([NH2:10])=[CH:8][C:7]([O:11][CH3:12])=[C:6]([O:13][CH3:14])[CH:5]=1)=O.B(F)(F)F.CCOCC.[CH:24]([NH2:26])=O>>[CH3:1][C:2]1[C:4]2[C:9](=[CH:8][C:7]([O:11][CH3:12])=[C:6]([O:13][CH3:14])[CH:5]=2)[N:10]=[CH:24][N:26]=1

Participants

4

Reactant 3

HCID 713FormamideHCID 8000Boron trifluoride etherateHCID 602085Ethanone, 1-(2-amino-4,5-dimethoxyphenyl)-

Product 1

HCID 43194226,7-Dimethoxy-4-methylquinazoline

Procedure

2-Amino-4,5-dimethoxyacetophenone (5.0 g) and boron trifluoride etherate (1.5 mL) were heated in formamide (80 mL) at 140° C. for 18 h. The reaction mixture was cooled to room temperature and extracted three times with benzene. The combined organic layers were dried over anhydrous sodium sulfate and concentrated under vacuum. Flash chromatography on silical gel, eluting with a mixture of 98/2 dichloromethane/methanol gave 4-methyl-6,7-dimethoxyquinazoline (D-1) as a yellow solid, 3.43 g; 1H NMR (CDCl3, 300 MHz) 8.99 (s, 1H), 7.30 (s, 1H), 7.18 (s, 1H), 4.05 (s, 6H), 2.87 (s, 1H) ppm; MS (ES) 205 (M+H).

Workup

  1. extractionextracted three times with benzene
  2. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  3. concentrationconcentrated under vacuum
  4. washFlash chromatography on silical gel, eluting with a mixture of 98/2 dichloromethane/methanol

Sources & evidence

ORD record
ord-dadbc6b86396436285eea0d2ae980974
Source dataset
uspto-grants-2012_10
Patent number
US08288382B2

Reaction notes

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