3-[(dimethylamino)methylene]-1-(5,6,7,8-tetrahydrobenzo[b]thieno[2,3-d]pyrimidin-4-yl)-4-oxocyclohexanecarbonitrile

Base Information

Chemical Name:3-[(dimethylamino)methylene]-1-(5,6,7,8-tetrahydrobenzo[b]thieno[2,3-d]pyrimidin-4-yl)-4-oxocyclohexanecarbonitrile
CAS No.:1392208-68-2
Molecular Formula:C₂₀H₂₂N₄OS
Molecular Weight:366.487
Hs Code.:

Synonyms:3-[(dimethylamino)methylene]-1-(5,6,7,8-tetrahydrobenzo[b]thieno[2,3-d]pyrimidin-4-yl)-4-oxocyclohexanecarbonitrile

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Chemical Property of 3-[(dimethylamino)methylene]-1-(5,6,7,8-tetrahydrobenzo[b]thieno[2,3-d]pyrimidin-4-yl)-4-oxocyclohexanecarbonitrile

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Technology Process of 3-[(dimethylamino)methylene]-1-(5,6,7,8-tetrahydrobenzo[b]thieno[2,3-d]pyrimidin-4-yl)-4-oxocyclohexanecarbonitrile

There total 5 articles about 3-[(dimethylamino)methylene]-1-(5,6,7,8-tetrahydrobenzo[b]thieno[2,3-d]pyrimidin-4-yl)-4-oxocyclohexanecarbonitrile 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: 64.0%

: 1392208-61-5
1-(5,6,7,8-tetrahydrobenzo[b]thieno[2,3-d]pyrimidin-4-yl)-4-oxocyclohexanecarbonitrile

: 4637-24-5
N,N-dimethyl-formamide dimethyl acetal

: 1392208-68-2
3-[(dimethylamino)methylene]-1-(5,6,7,8-tetrahydrobenzo[b]thieno[2,3-d]pyrimidin-4-yl)-4-oxocyclohexanecarbonitrile

Guidance literature:: With triethylamine; In N,N-dimethyl-formamide; at 110 ℃; for 4h; Inert atmosphere;
DOI:10.1039/c2ob25420d

Reference yield:

: 1392208-55-7
methyl-5-cyano-5-(5,6,7,8-tetrahydrobenzo[b]thieno[2,3-d]pyrimidin-4-yl)-2-oxocyclohexanecarboxylate

: 1392208-68-2
3-[(dimethylamino)methylene]-1-(5,6,7,8-tetrahydrobenzo[b]thieno[2,3-d]pyrimidin-4-yl)-4-oxocyclohexanecarbonitrile

Guidance literature:: Multi-step reaction with 2 steps

1: sodium chloride / water; dimethyl sulfoxide / 5 h / 150 °C / Inert atmosphere

2: triethylamine / N,N-dimethyl-formamide / 4 h / 110 °C / Inert atmosphere

With triethylamine; sodium chloride; In water; dimethyl sulfoxide; N,N-dimethyl-formamide; 1: Krapcho decarboxylation;
DOI:10.1039/c2ob25420d

Reference yield:

: 40493-18-3
4-chloro-5,6,7,8-tetrahydro[1]benzothieno[2,3-d]pyrimidine

: 1392208-68-2
3-[(dimethylamino)methylene]-1-(5,6,7,8-tetrahydrobenzo[b]thieno[2,3-d]pyrimidin-4-yl)-4-oxocyclohexanecarbonitrile

Guidance literature:: Multi-step reaction with 5 steps

1: potassium carbonate / 1.5 h / 60 - 140 °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

4: sodium chloride / water; dimethyl sulfoxide / 5 h / 150 °C / Inert atmosphere

5: triethylamine / N,N-dimethyl-formamide / 4 h / 110 °C / Inert atmosphere

With N-benzyl-trimethylammonium hydroxide; sodium hydride; potassium carbonate; triethylamine; sodium chloride; In 1,2-dimethoxyethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; acetonitrile; 2: Michael reaction / 3: Dieckmann cyclisation / 4: Krapcho decarboxylation;
DOI:10.1039/c2ob25420d