tert-butyl 4-[N-[7-chloro-2-hydroxymethyl-4-oxo-3,4-dihydroxyquinazolin-6-ylmethyl]-N-(prop-2-ynyl)amino]benzoate

Base Information

• Chemical Name: tert-butyl 4-[N-[7-chloro-2-hydroxymethyl-4-oxo-3,4-dihydroxyquinazolin-6-ylmethyl]-N-(prop-2-ynyl)amino]benzoate
• CAS No.: 289687-02-1
• Molecular Formula: C₂₄H₂₄ClN₃O₄
• Molecular Weight: 453.925

Synonyms:tert-butyl 4-[N-[7-chloro-2-hydroxymethyl-4-oxo-3,4-dihydroxyquinazolin-6-ylmethyl]-N-(prop-2-ynyl)amino]benzoate

Chemical Property of tert-butyl 4-[N-[7-chloro-2-hydroxymethyl-4-oxo-3,4-dihydroxyquinazolin-6-ylmethyl]-N-(prop-2-ynyl)amino]benzoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

Technology Process of tert-butyl 4-[N-[7-chloro-2-hydroxymethyl-4-oxo-3,4-dihydroxyquinazolin-6-ylmethyl]-N-(prop-2-ynyl)amino]benzoate

There total 10 articles about tert-butyl 4-[N-[7-chloro-2-hydroxymethyl-4-oxo-3,4-dihydroxyquinazolin-6-ylmethyl]-N-(prop-2-ynyl)amino]benzoate 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: 70.0%

tert-butyl 4-[N-[2-acetoxymethyl-7-chloro-4-oxo-3,4-dihydroxyquinazolin-6-ylmethyl]-N-(prop-2-ynyl)amino]benzoate (289687-01-0) → tert-butyl 4-[N-[7-chloro-2-hydroxymethyl-4-oxo-3,4-dihydroxyquinazolin-6-ylmethyl]-N-(prop-2-ynyl)amino]benzoate (289687-02-1)

Guidance literature:

With sodium hydroxide; In tetrahydrofuran; at 20 ℃; for 2h;

DOI:10.1021/jm011081s

Reference yield:

3-chloro-p-toluidine (95-74-9,827571-80-2) → tert-butyl 4-[N-[7-chloro-2-hydroxymethyl-4-oxo-3,4-dihydroxyquinazolin-6-ylmethyl]-N-(prop-2-ynyl)amino]benzoate (289687-02-1)

Guidance literature:

Multi-step reaction with 10 steps

1: 86 percent / pyridine / ethyl acetate / 18 h / 20 °C

2: 48 percent / glacial AcOH; Br₂ / 1.5 h / 15 °C

3: 94 percent / AcOH; conc. HCl / 24 h / 118 °C

4: 6.52 g / N-methylpyrrolidinone / 2 h / 163 °C

5: 93 percent / aq. KOH; H₂O₂ / 2 h / 130 °C

6: 69 percent / Na / methanol / 2 h / 20 °C

7: 87 percent / dimethylformamide / 2.25 h / 85 °C

8: 40 percent / NBS; dibenzoyl peroxide / CCl₄ / 3.5 h / 120 °C / Irradiation

9: 48 percent / 2,6-lutidine / dimethylformamide / 16 h / 120 °C

10: 70 percent / aq. NaOH / tetrahydrofuran / 2 h / 20 °C

With pyridine; 2,6-dimethylpyridine; 1-methyl-pyrrolidin-2-one; hydrogenchloride; potassium hydroxide; sodium hydroxide; N-Bromosuccinimide; dihydrogen peroxide; bromine; sodium; acetic acid; dibenzoyl peroxide; In tetrahydrofuran; methanol; tetrachloromethane; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1021/jm011081s

Reference yield:

N-(3-chloro-4-methylphenyl)acetamide (7149-79-3) → tert-butyl 4-[N-[7-chloro-2-hydroxymethyl-4-oxo-3,4-dihydroxyquinazolin-6-ylmethyl]-N-(prop-2-ynyl)amino]benzoate (289687-02-1)

Guidance literature:

Multi-step reaction with 9 steps

1: 48 percent / glacial AcOH; Br₂ / 1.5 h / 15 °C

2: 94 percent / AcOH; conc. HCl / 24 h / 118 °C

3: 6.52 g / N-methylpyrrolidinone / 2 h / 163 °C

4: 93 percent / aq. KOH; H₂O₂ / 2 h / 130 °C

5: 69 percent / Na / methanol / 2 h / 20 °C

6: 87 percent / dimethylformamide / 2.25 h / 85 °C

7: 40 percent / NBS; dibenzoyl peroxide / CCl₄ / 3.5 h / 120 °C / Irradiation

8: 48 percent / 2,6-lutidine / dimethylformamide / 16 h / 120 °C

9: 70 percent / aq. NaOH / tetrahydrofuran / 2 h / 20 °C

With 2,6-dimethylpyridine; 1-methyl-pyrrolidin-2-one; hydrogenchloride; potassium hydroxide; sodium hydroxide; N-Bromosuccinimide; dihydrogen peroxide; bromine; sodium; acetic acid; dibenzoyl peroxide; In tetrahydrofuran; methanol; tetrachloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm011081s

upstream raw materials:

tert-butyl 4-[N-[2-acetoxymethyl-7-chloro-4-oxo-3,4-dihydroxyquinazolin-6-ylmethyl]-N-(prop-2-ynyl)amino]benzoate

N-(3-chloro-4-methylphenyl)acetamide

2-bromo-5-chloro-4-methylaniline

N-(2-bromo-5-chloro-4-methylphenyl)acetamide

Downstream raw materials:

tert-butyl 4-[N-[7-chloro-2-methanesulfonyloxymethyl-4-oxo-3,4-dihydroxyquinazolin-6-ylmethyl]-N-(prop-2-ynyl)amino]benzoate

tert-butyl 4-[N-[7-chloro-4-oxo-2-piperidin-1-ylmethyl-3-piperidinocarbonylmethyl-3,4-dihydroquinazolin-6-ylmethyl]-N-(prop-2-ynyl)amino]benzoate

4-{[7-chloro-4-oxo-3-(2-oxo-2-piperidin-1-yl-ethyl)-2-piperidin-1-ylmethyl-3,4-dihydro-quinazolin-6-ylmethyl]-prop-2-ynyl-amino}-benzoic acid

tert-butyl 4-[N-[7-chloro-3-diethylcarbamoylmethyl-4-oxo-2-piperidin-1-ylmethyl-3,4-dihydroquinazolin-6-ylmethyl]-N-(prop-2-ynyl)amino]benzoate

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