methyl 3-(3-chloro-4-fluorobenzyl)-5-methoxy-4-oxo-3,4-dihydropyrido[3,4-d]pyrimidin-8-carboxylate

Base Information

• Chemical Name: methyl 3-(3-chloro-4-fluorobenzyl)-5-methoxy-4-oxo-3,4-dihydropyrido[3,4-d]pyrimidin-8-carboxylate
• CAS No.: 1202013-34-0
• Molecular Formula: C₁₇H₁₃ClFN₃O₄
• Molecular Weight: 377.759
• Mol file: 1202013-34-0.mol

Synonyms:methyl 3-(3-chloro-4-fluorobenzyl)-5-methoxy-4-oxo-3,4-dihydropyrido[3,4-d]pyrimidin-8-carboxylate

Chemical Property of methyl 3-(3-chloro-4-fluorobenzyl)-5-methoxy-4-oxo-3,4-dihydropyrido[3,4-d]pyrimidin-8-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 3-(3-chloro-4-fluorobenzyl)-5-methoxy-4-oxo-3,4-dihydropyrido[3,4-d]pyrimidin-8-carboxylate

There total 10 articles about methyl 3-(3-chloro-4-fluorobenzyl)-5-methoxy-4-oxo-3,4-dihydropyrido[3,4-d]pyrimidin-8-carboxylate 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:

methanol (67-56-1) + carbon monoxide (201230-82-2) + 3-(3-chloro-4-fluorobenzyl)-5-methoxy-4-oxo-3,4-dihydropyrido[3,4-d]pyrimidin-8-yl trifluoromethanesulfonate (1202013-32-8) → methyl 3-(3-chloro-4-fluorobenzyl)-5-methoxy-4-oxo-3,4-dihydropyrido[3,4-d]pyrimidin-8-carboxylate (1202013-34-0)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; palladium diacetate; In dimethyl sulfoxide; at 80 ℃; for 24h; under 15514.9 Torr;

Reference yield:

3-bromo-5-methoxypyridine (50720-12-2) → methyl 3-(3-chloro-4-fluorobenzyl)-5-methoxy-4-oxo-3,4-dihydropyrido[3,4-d]pyrimidin-8-carboxylate (1202013-34-0)

Guidance literature:

Multi-step reaction with 10 steps

1.1: caesium carbonate / tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene / 1,4-dioxane / 72 h / 90 °C

2.1: n-butyllithium / tetrahydrofuran; hexane / -78 - -25 °C

2.2: -78 °C

3.1: trifluoroacetic acid / dichloromethane / 3 h / 20 °C

4.1: ethanol / 48 h / Reflux

5.1: caesium carbonate / N,N-dimethyl-formamide / 4 h / 20 °C

6.1: peracetic acid; sodium acetate; acetic acid / 12 h / 20 °C

7.1: 0.33 h / 130 °C / Microwave irradiation

8.1: water; sodium hydroxide / methanol / 2 h / 20 °C

9.1: 2,6-dimethylpyridine; dmap / dichloromethane / 14 h / 20 °C

10.1: N-ethyl-N,N-diisopropylamine / palladium diacetate / dimethyl sulfoxide / 24 h / 80 °C / 15514.9 Torr

With 2,6-dimethylpyridine; peracetic acid; dmap; n-butyllithium; water; sodium acetate; caesium carbonate; acetic acid; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; sodium hydroxide; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; palladium diacetate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In tetrahydrofuran; 1,4-dioxane; methanol; ethanol; hexane; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide;

Reference yield:

tert-butyl 5-methoxypyridin-3-ylcarbamate (342603-10-5) → methyl 3-(3-chloro-4-fluorobenzyl)-5-methoxy-4-oxo-3,4-dihydropyrido[3,4-d]pyrimidin-8-carboxylate (1202013-34-0)

Guidance literature:

Multi-step reaction with 9 steps

1.1: n-butyllithium / tetrahydrofuran; hexane / -78 - -25 °C

1.2: -78 °C

2.1: trifluoroacetic acid / dichloromethane / 3 h / 20 °C

3.1: ethanol / 48 h / Reflux

4.1: caesium carbonate / N,N-dimethyl-formamide / 4 h / 20 °C

5.1: peracetic acid; sodium acetate; acetic acid / 12 h / 20 °C

6.1: 0.33 h / 130 °C / Microwave irradiation

7.1: water; sodium hydroxide / methanol / 2 h / 20 °C

8.1: 2,6-dimethylpyridine; dmap / dichloromethane / 14 h / 20 °C

9.1: N-ethyl-N,N-diisopropylamine / palladium diacetate / dimethyl sulfoxide / 24 h / 80 °C / 15514.9 Torr

With 2,6-dimethylpyridine; peracetic acid; dmap; n-butyllithium; water; sodium acetate; caesium carbonate; acetic acid; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; sodium hydroxide; palladium diacetate; In tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide;

upstream raw materials:

methanol

carbon monoxide

3-(3-chloro-4-fluorobenzyl)-5-methoxy-4-oxo-3,4-dihydropyrido[3,4-d]pyrimidin-8-yl trifluoromethanesulfonate

3-bromo-5-methoxypyridine

Downstream raw materials:

3-(3-chloro-4-fluorobenzyl)-5-hydroxy-12-methyl-9,10,11,12-tetrahydro-3H-pyridazino[4',5':3,4]pyrido[1,2-a][1,4]diazocine-4,6,13(8H)-trione

methyl 3-(3-chloro-4-fluorobenzyl)-5-methoxy-4-oxo-3,4-dihydropyrido[3,4-d]pyrimidin-8-carboxylate-7-oxide

methyl 6-(acetyloxy)-3-(3-chloro-4-fluorobenzyl)-5-methoxy-4-oxo-3,4-dihydropyrido[3,4-d]pyrimidin-8-carboxylate

3-(3-chloro-4-fluorobenzyl)-6-hydroxy-5-methoxy-4-oxo-3,4-dihydropyrido[3,4-d]pyrimidine-8-carboxylic acid