tert-butyl 4-(((2-(acetoxyMethyl)-7-chloro-3-Methyl-4-oxo-3,4-dihydroquinazolin-6-yl)Methyl)(prop-2-ynyl)aMino)benzoate

Base Information

• Chemical Name: tert-butyl 4-(((2-(acetoxyMethyl)-7-chloro-3-Methyl-4-oxo-3,4-dihydroquinazolin-6-yl)Methyl)(prop-2-ynyl)aMino)benzoate
• CAS No.: 289686-87-9
• Molecular Formula: C₂₇H₂₈ClN₃O₅
• Molecular Weight: 509.989
• Mol file: 289686-87-9.mol

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

Chemical Property of tert-butyl 4-(((2-(acetoxyMethyl)-7-chloro-3-Methyl-4-oxo-3,4-dihydroquinazolin-6-yl)Methyl)(prop-2-ynyl)aMino)benzoate

Chemical Property:

Purity/Quality:

≥95% ^*data from raw suppliers

tert-butyl4-(((2-(acetoxymethyl)-7-chloro-3-methyl-4-oxo-3,4-dihydroquinazolin-6-yl)methyl)(prop-2-ynyl)amino)benzoate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of tert-butyl 4-(((2-(acetoxyMethyl)-7-chloro-3-Methyl-4-oxo-3,4-dihydroquinazolin-6-yl)Methyl)(prop-2-ynyl)aMino)benzoate

There total 15 articles about tert-butyl 4-(((2-(acetoxyMethyl)-7-chloro-3-Methyl-4-oxo-3,4-dihydroquinazolin-6-yl)Methyl)(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: 73.0%

tert-butyl p-[N-(prop-2-ynyl)amino]benzoate (112888-76-3) + 2-acetoxymethyl-6-bromomethyl-7-chloro-3-methyl-3,4-dihydroquinazolin-4-one (289686-86-8) → tert-butyl 4-[N-[2-acetoxymethyl-7-chloro-3-methyl-4-oxo-3,4-dihydroquinazolin-6-ylmethyl]-N-(prop-2-ynyl)amino]benzoate (289686-87-9)

Guidance literature:

With 2,6-dimethylpyridine; In N,N-dimethyl-formamide; at 120 ℃; for 5.5h;

DOI:10.1021/jm011081s

Reference yield:

3-chloro-p-toluidine (95-74-9,827571-80-2) → tert-butyl 4-[N-[2-acetoxymethyl-7-chloro-3-methyl-4-oxo-3,4-dihydroquinazolin-6-ylmethyl]-N-(prop-2-ynyl)amino]benzoate (289686-87-9)

Guidance literature:

Multi-step reaction with 13 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: 97 percent / tetrahydrofuran / 6 h / 20 °C

7: 90 percent / DMAP / 3 h / 80 °C

8: 90 percent / pyridine / dimethylformamide / 2 h / 20 °C

9: 0.230 g / methanol; tetrahydrofuran / 26 h / 20 °C

10: 76 percent / 48percent aq. HBr / 7 h / 120 °C

11: 98 percent / DMAP; Et₃N / CH₂Cl₂ / 0.5 h / 20 °C

12: 51 percent / NBS; dibenzoyl peroxide / CCl₄ / 3.83 h / 85 °C / Irradiation

13: 73 percent / 2,6-lutidine / dimethylformamide / 5.5 h / 120 °C

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

DOI:10.1021/jm011081s

Reference yield:

2-bromo-5-chloro-4-methylaniline (102170-52-5) → tert-butyl 4-[N-[2-acetoxymethyl-7-chloro-3-methyl-4-oxo-3,4-dihydroquinazolin-6-ylmethyl]-N-(prop-2-ynyl)amino]benzoate (289686-87-9)

Guidance literature:

Multi-step reaction with 10 steps

1: 6.52 g / N-methylpyrrolidinone / 2 h / 163 °C

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

3: 97 percent / tetrahydrofuran / 6 h / 20 °C

4: 90 percent / DMAP / 3 h / 80 °C

5: 90 percent / pyridine / dimethylformamide / 2 h / 20 °C

6: 0.230 g / methanol; tetrahydrofuran / 26 h / 20 °C

7: 76 percent / 48percent aq. HBr / 7 h / 120 °C

8: 98 percent / DMAP; Et₃N / CH₂Cl₂ / 0.5 h / 20 °C

9: 51 percent / NBS; dibenzoyl peroxide / CCl₄ / 3.83 h / 85 °C / Irradiation

10: 73 percent / 2,6-lutidine / dimethylformamide / 5.5 h / 120 °C

With pyridine; 2,6-dimethylpyridine; 1-methyl-pyrrolidin-2-one; dmap; potassium hydroxide; N-Bromosuccinimide; dihydrogen peroxide; triethylamine; dibenzoyl peroxide; In tetrahydrofuran; methanol; tetrachloromethane; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm011081s

upstream raw materials:

tert-butyl p-[N-(prop-2-ynyl)amino]benzoate

2-acetoxymethyl-6-bromomethyl-7-chloro-3-methyl-3,4-dihydroquinazolin-4-one

2-bromo-5-chloro-4-methylaniline

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

Downstream raw materials:

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

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

CB 300919

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

Refernces

• 1、 Bavetsias,Skelton,Yafai,Mitchell,Wilson,Allan,Jackman. "The design and synthesis of water-soluble analogues of CB30865, a quinazolin-4-one-based antitumor agent". . p. 3692 - 3702. Retrieved 2007/10/03.