4-[(2-Amino-4-oxo-3,4,5,6,7,8-hexahydro-quinazolin-6-ylmethyl)-methyl-amino]-benzoic acid

Base Information

• Chemical Name: 4-[(2-Amino-4-oxo-3,4,5,6,7,8-hexahydro-quinazolin-6-ylmethyl)-methyl-amino]-benzoic acid
• CAS No.: 107174-50-5
• Molecular Formula: C₁₇H₂₀N₄O₃
• Molecular Weight: 328.371

Synonyms:4-[(2-Amino-4-oxo-3,4,5,6,7,8-hexahydro-quinazolin-6-ylmethyl)-methyl-amino]-benzoic acid

Chemical Property of 4-[(2-Amino-4-oxo-3,4,5,6,7,8-hexahydro-quinazolin-6-ylmethyl)-methyl-amino]-benzoic acid

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Technology Process of 4-[(2-Amino-4-oxo-3,4,5,6,7,8-hexahydro-quinazolin-6-ylmethyl)-methyl-amino]-benzoic acid

There total 4 articles about 4-[(2-Amino-4-oxo-3,4,5,6,7,8-hexahydro-quinazolin-6-ylmethyl)-methyl-amino]-benzoic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 38.0%

N-methyl-p-aminobenzoic acid (10541-83-0,937737-33-2) + 2-amino-6-(bromomethyl)-4-hydroxy-5,6,7,8-tetrahydroquinazoline hydrobromide (107174-53-8) → 4-[(2-Amino-4-oxo-3,4,5,6,7,8-hexahydro-quinazolin-6-ylmethyl)-methyl-amino]-benzoic acid (107174-50-5)

Guidance literature:

With magnesium oxide; In N,N-dimethyl acetamide; at 120 - 135 ℃; for 18h;

DOI:10.1021/jm00390a025

Reference yield:

2-amino-6-hydroxymethyl-5,6,7,8-tetrahydro-3H-quinazolin-4-one (5452-19-7) → 4-[(2-Amino-4-oxo-3,4,5,6,7,8-hexahydro-quinazolin-6-ylmethyl)-methyl-amino]-benzoic acid (107174-50-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 3.5 g / 49percent aq. HBr / 4 h / Heating

2: 38 percent / MgO / N,N-dimethyl-acetamide / 18 h / 120 - 135 °C

With hydrogen bromide; magnesium oxide; In N,N-dimethyl acetamide;

DOI:10.1021/jm00390a025

Reference yield:

2-amino-6-carbo-n-butoxy-4-hydroxy-5,6,7,8-tetrahydroquinazoline (5446-29-7) → 4-[(2-Amino-4-oxo-3,4,5,6,7,8-hexahydro-quinazolin-6-ylmethyl)-methyl-amino]-benzoic acid (107174-50-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 5.74 g / CF₃COOH / 7 h

2: 982 mg / lithium triethylborohydride / tetrahydrofuran / 2 h

3: 3.5 g / 49percent aq. HBr / 4 h / Heating

4: 38 percent / MgO / N,N-dimethyl-acetamide / 18 h / 120 - 135 °C

With hydrogen bromide; magnesium oxide; lithium triethylborohydride; trifluoroacetic acid; In tetrahydrofuran; N,N-dimethyl acetamide;

DOI:10.1021/jm00390a025

upstream raw materials:

N-methyl-p-aminobenzoic acid

2-amino-6-(bromomethyl)-4-hydroxy-5,6,7,8-tetrahydroquinazoline hydrobromide

2-amino-6-hydroxymethyl-5,6,7,8-tetrahydro-3H-quinazolin-4-one

2-amino-6-carbo-n-butoxy-4-hydroxy-5,6,7,8-tetrahydroquinazoline

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