tert-Butyl 4-[N-[7-Chloro-2-hydroxymethyl-3-methyl-4-oxo-3,4-dihydroquinazolin-6-ylmethyl]-N-(prop-2-ynyl)amino]benzoate

Base Information

• Chemical Name: tert-Butyl 4-[N-[7-Chloro-2-hydroxymethyl-3-methyl-4-oxo-3,4-dihydroquinazolin-6-ylmethyl]-N-(prop-2-ynyl)amino]benzoate
• CAS No.: 289686-88-0
• Molecular Formula: C₂₅H₂₆ClN₃O₄
• Molecular Weight: 467.952
• DSSTox Substance ID: DTXSID001103281
• Mol file: 289686-88-0.mol

Synonyms:SCHEMBL6582221;LQZYAHFKKVHFDS-UHFFFAOYSA-N;DTXSID001103281;1,1-Dimethylethyl 4-[[[7-chloro-3,4-dihydro-2-(hydroxymethyl)-3-methyl-4-oxo-6-quinazolinyl]methyl]-2-propyn-1-ylamino]benzoate;289686-88-0;tert-Butyl 4-[N-[7-Chloro-2-hydroxymethyl-3-methyl-4-oxo-3,4-dihydroquinazolin-6-ylmethyl]-N-(prop-2-ynyl)amino]benzoate

Chemical Property of tert-Butyl 4-[N-[7-Chloro-2-hydroxymethyl-3-methyl-4-oxo-3,4-dihydroquinazolin-6-ylmethyl]-N-(prop-2-ynyl)amino]benzoate

Chemical Property:

• XLogP3: 3.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 8
• Exact Mass: 467.1611840
• Heavy Atom Count: 33
• Complexity: 806

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)C1=CC=C(C=C1)N(CC#C)CC2=CC3=C(C=C2Cl)N=C(N(C3=O)C)CO

Technology Process of tert-Butyl 4-[N-[7-Chloro-2-hydroxymethyl-3-methyl-4-oxo-3,4-dihydroquinazolin-6-ylmethyl]-N-(prop-2-ynyl)amino]benzoate

There total 16 articles about tert-Butyl 4-[N-[7-Chloro-2-hydroxymethyl-3-methyl-4-oxo-3,4-dihydroquinazolin-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: 80.0%

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) → tert-butyl 4-[N-[7-chloro-2-hydroxymethyl-3-methyl-4-oxo-3,4-dihydroquinazolin-6-ylmethyl]-N-(prop-2-ynyl)amino]benzoate (289686-88-0)

Guidance literature:

With sodium hydroxide; In tetrahydrofuran; at 20 ℃; for 1h;

DOI:10.1021/jm011081s

Reference yield:

3-chloro-p-toluidine (95-74-9,827571-80-2) → tert-butyl 4-[N-[7-chloro-2-hydroxymethyl-3-methyl-4-oxo-3,4-dihydroquinazolin-6-ylmethyl]-N-(prop-2-ynyl)amino]benzoate (289686-88-0)

Guidance literature:

Multi-step reaction with 14 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

14: 80 percent / aq. NaOH / tetrahydrofuran / 1 h / 20 °C

With pyridine; 2,6-dimethylpyridine; 1-methyl-pyrrolidin-2-one; hydrogenchloride; dmap; potassium hydroxide; sodium 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-[7-chloro-2-hydroxymethyl-3-methyl-4-oxo-3,4-dihydroquinazolin-6-ylmethyl]-N-(prop-2-ynyl)amino]benzoate (289686-88-0)

Guidance literature:

Multi-step reaction with 11 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

11: 80 percent / aq. NaOH / tetrahydrofuran / 1 h / 20 °C

With pyridine; 2,6-dimethylpyridine; 1-methyl-pyrrolidin-2-one; dmap; potassium hydroxide; sodium 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 4-[N-[2-acetoxymethyl-7-chloro-3-methyl-4-oxo-3,4-dihydroquinazolin-6-ylmethyl]-N-(prop-2-ynyl)amino]benzoate

2-bromo-5-chloro-4-methylaniline

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

2-amino-5-methyl-4-chlorobenzoic acid

Downstream raw materials:

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

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

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