methyl 6-amino-2,3,4-trimethoxybenzoate

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of methyl 6-amino-2,3,4-tris(methyloxy)benzoate (2.87 g, 11.90 mmol) and formamidine acetate (3.72 g, 35.7 mmol) in 2-methoxyethanol (25 mL) was stirred at 125° C. for 2 hrs before being concentrated. The residue was suspended in water and the solid was collected by filtration, washed with water, and dried under vacuum (45° C.) to give 5,6,7-tris(methyloxy)-4(1H)-quinazolinone (1 g, 34%) as a light brown solid. MS (m/z) 237.1 (M+H+). before being concentrated the solid was collected by filtration washed with water dried under vacuum (45° C.)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 6-amino-2,3,4-tris(methyloxy)benzoic acid (2.7 g, 11.88 mmol) in THF (20 mL) and MeOH (20 mL) at 25° C. was treated with a solution of 2M TMS-diazomethane in Et2O (14.85 mL, 29.7 mmol) and stirred for 10 minutes before being concentrated to give methyl 6-amino-2,3,4-tris(methyloxy)benzoate (2.87 g, 99%) as a brown solid. MS (m/z) 242.1 (M+H+). before being concentrated

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of methyl 6-amino-2,3,4-tris(methyloxy)benzoate (2.87 g, 11.90 mmol) and formamidine acetate (3.72 g, 35.7 mmol) in 2-methoxyethanol (25 mL) was stirred at 125° C. for 2 hrs before being concentrated. The residue was suspended in water and the solid was collected by filtration, washed with water, and dried under vacuum (45° C.) to give 5,6,7-tris(methyloxy)-4(1H)-quinazolinone (1 g, 34%) as a light brown solid. MS (m/z) 237.1 (M+H+). before being concentrated the solid was collected by filtration washed with water dried under vacuum (45° C.)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 6-amino-2,3,4-tris(methyloxy)benzoic acid (2.7 g, 11.88 mmol) in THF (20 mL) and MeOH (20 mL) at 25° C. was treated with a solution of 2M TMS-diazomethane in Et2O (14.85 mL, 29.7 mmol) and stirred for 10 minutes before being concentrated to give methyl 6-amino-2,3,4-tris(methyloxy)benzoate (2.87 g, 99%) as a brown solid. MS (m/z) 242.1 (M+H+). before being concentrated