methyl-5-cyano-5-(6,7,8,9-tetrahydro-5H-cyclohepta[4,5]thieno[2,3-d]pyrimidin-4-yl)-2-oxocyclohexanecarboxylate

Base Information

• Chemical Name: methyl-5-cyano-5-(6,7,8,9-tetrahydro-5H-cyclohepta[4,5]thieno[2,3-d]pyrimidin-4-yl)-2-oxocyclohexanecarboxylate
• CAS No.: 1392208-58-0
• Molecular Formula: C₂₀H₂₁N₃O₃S
• Molecular Weight: 383.471
• Mol file: 1392208-58-0.mol

Synonyms:methyl-5-cyano-5-(6,7,8,9-tetrahydro-5H-cyclohepta[4,5]thieno[2,3-d]pyrimidin-4-yl)-2-oxocyclohexanecarboxylate

Chemical Property of methyl-5-cyano-5-(6,7,8,9-tetrahydro-5H-cyclohepta[4,5]thieno[2,3-d]pyrimidin-4-yl)-2-oxocyclohexanecarboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl-5-cyano-5-(6,7,8,9-tetrahydro-5H-cyclohepta[4,5]thieno[2,3-d]pyrimidin-4-yl)-2-oxocyclohexanecarboxylate

There total 4 articles about methyl-5-cyano-5-(6,7,8,9-tetrahydro-5H-cyclohepta[4,5]thieno[2,3-d]pyrimidin-4-yl)-2-oxocyclohexanecarboxylate 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: 72.0%

4-cyano-4-(6,7,8,9-tetrahydro-5H-cyclohepta[4,5]-thieno[2,3-d]pyrimidin-4-yl)-heptanedioic acid dimethyl ester (1392208-50-2) → methyl-5-cyano-5-(6,7,8,9-tetrahydro-5H-cyclohepta[4,5]thieno[2,3-d]pyrimidin-4-yl)-2-oxocyclohexanecarboxylate (1392208-58-0)

Guidance literature:

With sodium hydride; In 1,2-dimethoxyethane; at 0 - 70 ℃; for 2.5h; Inert atmosphere;

DOI:10.1039/c2ob25420d

Reference yield:

ethyl 2-cyano-2-(6,7,8,9-tetrahydro-5H-cyclohepta[4,5]thieno[2,3-d]pyrimidin-4-yl)acetate (1392208-38-6) → methyl-5-cyano-5-(6,7,8,9-tetrahydro-5H-cyclohepta[4,5]thieno[2,3-d]pyrimidin-4-yl)-2-oxocyclohexanecarboxylate (1392208-58-0)

Guidance literature:

Multi-step reaction with 3 steps

1: sodium chloride / water; dimethyl sulfoxide / 4.5 h / 150 °C / Inert atmosphere

2: N-benzyl-trimethylammonium hydroxide / acetonitrile / 3 h / Reflux; Inert atmosphere

3: sodium hydride / 1,2-dimethoxyethane / 2.5 h / 0 - 70 °C / Inert atmosphere

With N-benzyl-trimethylammonium hydroxide; sodium hydride; sodium chloride; In 1,2-dimethoxyethane; water; dimethyl sulfoxide; acetonitrile; 2: Michael reaction / 3: Dieckmann cyclisation;

DOI:10.1039/c2ob25420d

Reference yield:

2-(6,7,8,9-tetrahydro-5H-cyclohepta[4,5]thieno-[2,3-d]pyrimidin-4-yl)acetonitrile (1392208-44-4) → methyl-5-cyano-5-(6,7,8,9-tetrahydro-5H-cyclohepta[4,5]thieno[2,3-d]pyrimidin-4-yl)-2-oxocyclohexanecarboxylate (1392208-58-0)

Guidance literature:

Multi-step reaction with 2 steps

1: N-benzyl-trimethylammonium hydroxide / acetonitrile / 3 h / Reflux; Inert atmosphere

2: sodium hydride / 1,2-dimethoxyethane / 2.5 h / 0 - 70 °C / Inert atmosphere

With N-benzyl-trimethylammonium hydroxide; sodium hydride; In 1,2-dimethoxyethane; acetonitrile; 1: Michael reaction / 2: Dieckmann cyclisation;

DOI:10.1039/c2ob25420d

upstream raw materials:

ethyl 2-cyano-2-(6,7,8,9-tetrahydro-5H-cyclohepta[4,5]thieno[2,3-d]pyrimidin-4-yl)acetate

2-(6,7,8,9-tetrahydro-5H-cyclohepta[4,5]thieno-[2,3-d]pyrimidin-4-yl)acetonitrile

4-cyano-4-(6,7,8,9-tetrahydro-5H-cyclohepta[4,5]-thieno[2,3-d]pyrimidin-4-yl)-heptanedioic acid dimethyl ester

4-chloro-6,7,8,9-tetrahydro-5H-cyclohepta[4,5]thieno[2,3- d]pyrimidine

Downstream raw materials:

1-(6,7,8,9-tetrahydro-5H-cyclohepta[4,5]thieno[2,3-d]pyrimidin-4-yl)-4-oxocyclohexanecarbonitrile

3-[(dimethylamino)methylene]-1-(6,7,8,9-tetrahydro-5H-cyclohepta[4,5]thieno[2,3-d]pyrimidin-4-yl)-4-oxocyclohexanecarbonitrile