dimethyl 4,6,10-trimethoxy-11-methyl-1-p-tolyl-15-oxa-3,5-diaza-tricyclo[6.6.1.0(2,7)]pentadeca-2⁽⁷⁾,3,5,8,10,13-hexaene-13,14-dicarboxylate

Base Information

• Chemical Name: dimethyl 4,6,10-trimethoxy-11-methyl-1-p-tolyl-15-oxa-3,5-diaza-tricyclo[6.6.1.0(2,7)]pentadeca-2⁽⁷⁾,3,5,8,10,13-hexaene-13,14-dicarboxylate
• CAS No.: 1339872-39-7
• Molecular Formula: C₂₇H₂₈N₂O₈
• Molecular Weight: 508.528

Synonyms:dimethyl 4,6,10-trimethoxy-11-methyl-1-p-tolyl-15-oxa-3,5-diaza-tricyclo[6.6.1.0(2,7)]pentadeca-2⁽⁷⁾,3,5,8,10,13-hexaene-13,14-dicarboxylate

Chemical Property of dimethyl 4,6,10-trimethoxy-11-methyl-1-p-tolyl-15-oxa-3,5-diaza-tricyclo[6.6.1.0(2,7)]pentadeca-2⁽⁷⁾,3,5,8,10,13-hexaene-13,14-dicarboxylate

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Technology Process of dimethyl 4,6,10-trimethoxy-11-methyl-1-p-tolyl-15-oxa-3,5-diaza-tricyclo[6.6.1.0(2,7)]pentadeca-2⁽⁷⁾,3,5,8,10,13-hexaene-13,14-dicarboxylate

There total 3 articles about dimethyl 4,6,10-trimethoxy-11-methyl-1-p-tolyl-15-oxa-3,5-diaza-tricyclo[6.6.1.0(2,7)]pentadeca-2⁽⁷⁾,3,5,8,10,13-hexaene-13,14-dicarboxylate 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: 82.0%

pentacarbonyl{methoxy(2-propenyl)carbene}chromium + (5-ethynyl-2,6-dimethoxypyrimidin-4-yl)p-tolylmethanone (1339872-34-2) + dimethyl acetylenedicarboxylate (762-42-5) → dimethyl 4,6,10-trimethoxy-11-methyl-1-p-tolyl-15-oxa-3,5-diaza-tricyclo[6.6.1.0(2,7)]pentadeca-2(7),3,5,8,10,13-hexaene-13,14-dicarboxylate (1339872-39-7)

Guidance literature:

pentacarbonyl{methoxy(2-propenyl)carbene}chromium; (5-ethynyl-2,6-dimethoxypyrimidin-4-yl)p-tolylmethanone; In tetrahydrofuran; for 0.25h; Inert atmosphere; Reflux;

dimethyl acetylenedicarboxylate; In tetrahydrofuran; for 2h; Inert atmosphere; Reflux;

DOI:10.1016/j.tetlet.2011.08.094

Reference yield:

(5-bromo-2,6-dimethoxypyrimidin-4-yl)(p-tolyl)methanone (1322681-61-7) → dimethyl 4,6,10-trimethoxy-11-methyl-1-p-tolyl-15-oxa-3,5-diaza-tricyclo[6.6.1.0(2,7)]pentadeca-2(7),3,5,8,10,13-hexaene-13,14-dicarboxylate (1339872-39-7)

Guidance literature:

Multi-step reaction with 3 steps

1.1: copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride; triethylamine; triphenylphosphine / tetrahydrofuran / 20 °C / Inert atmosphere

2.1: methanol; potassium carbonate / 0.5 h / 0 °C / Inert atmosphere

3.1: tetrahydrofuran / 0.25 h / Inert atmosphere; Reflux

3.2: 2 h / Inert atmosphere; Reflux

With methanol; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; potassium carbonate; triethylamine; triphenylphosphine; In tetrahydrofuran; 1.1: Sonogashira coupling / 3.2: Diels-Alder reaction;

DOI:10.1016/j.tetlet.2011.08.094

Reference yield:

{2,6-dimethoxy-5-[(trimethylsilyl)ethynyl]pyrimidin-4-yl}(p-tolyl)methanone (1322681-63-9) → dimethyl 4,6,10-trimethoxy-11-methyl-1-p-tolyl-15-oxa-3,5-diaza-tricyclo[6.6.1.0(2,7)]pentadeca-2(7),3,5,8,10,13-hexaene-13,14-dicarboxylate (1339872-39-7)

Guidance literature:

Multi-step reaction with 2 steps

1.1: methanol; potassium carbonate / 0.5 h / 0 °C / Inert atmosphere

2.1: tetrahydrofuran / 0.25 h / Inert atmosphere; Reflux

2.2: 2 h / Inert atmosphere; Reflux

With methanol; potassium carbonate; In tetrahydrofuran; 2.2: Diels-Alder reaction;

DOI:10.1016/j.tetlet.2011.08.094

upstream raw materials:

(5-ethynyl-2,6-dimethoxypyrimidin-4-yl)p-tolylmethanone

dimethyl acetylenedicarboxylate

(5-bromo-2,6-dimethoxypyrimidin-4-yl)(p-tolyl)methanone

{2,6-dimethoxy-5-[(trimethylsilyl)ethynyl]pyrimidin-4-yl}(p-tolyl)methanone

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