(E)-N-(4-((3-chloro-4-fluorophenyl)amino)thieno[2,3-d]pyrimidin-6-yl)-4-(3-hydroxyazetidin-1-yl)but-2-enamide

Base Information

Chemical Name:(E)-N-(4-((3-chloro-4-fluorophenyl)amino)thieno[2,3-d]pyrimidin-6-yl)-4-(3-hydroxyazetidin-1-yl)but-2-enamide
CAS No.:1595285-90-7
Molecular Formula:C₁₉H₁₇ClFN₅O₂S
Molecular Weight:433.894
Hs Code.:

Synonyms:(E)-N-(4-((3-chloro-4-fluorophenyl)amino)thieno[2,3-d]pyrimidin-6-yl)-4-(3-hydroxyazetidin-1-yl)but-2-enamide

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Chemical Property of (E)-N-(4-((3-chloro-4-fluorophenyl)amino)thieno[2,3-d]pyrimidin-6-yl)-4-(3-hydroxyazetidin-1-yl)but-2-enamide

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Technology Process of (E)-N-(4-((3-chloro-4-fluorophenyl)amino)thieno[2,3-d]pyrimidin-6-yl)-4-(3-hydroxyazetidin-1-yl)but-2-enamide

There total 6 articles about (E)-N-(4-((3-chloro-4-fluorophenyl)amino)thieno[2,3-d]pyrimidin-6-yl)-4-(3-hydroxyazetidin-1-yl)but-2-enamide 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: 71.0%

: 45347-82-8
azetidine-3-ol

: 13991-36-1
4-bromocrotonic acid

: 1595286-21-7
N⁴-(3-chloro-4-fluorophenyl)thieno[2,3-d]pyrimidine-4,6-diamine

: 1595285-90-7
(E)-N-(4-((3-chloro-4-fluorophenyl)amino)thieno[2,3-d]pyrimidin-6-yl)-4-(3-hydroxyazetidin-1-yl)but-2-enamide

Guidance literature:: 4-bromocrotonic acid; With thionyl chloride; In dichloromethane; at 20 ℃;

N⁴-(3-chloro-4-fluorophenyl)thieno[2,3-d]pyrimidine-4,6-diamine; With pyridine; In tetrahydrofuran; at 0 - 20 ℃;

azetidine-3-ol; With sodium iodide; In N,N-dimethyl-formamide; at 0 - 20 ℃;
DOI:10.1016/j.bmc.2014.01.035

Reference yield:

: 56844-41-8
6-nitrothieno[2,3-d]pyrimidin-4-ol

: 1595285-90-7
(E)-N-(4-((3-chloro-4-fluorophenyl)amino)thieno[2,3-d]pyrimidin-6-yl)-4-(3-hydroxyazetidin-1-yl)but-2-enamide

Guidance literature:: Multi-step reaction with 4 steps

1.1: trichlorophosphate; triethylamine / acetonitrile / 3 h / 70 °C

2.1: isopropyl alcohol / 2 h / 20 - 80 °C

3.1: iron; ammonium chloride / ethanol / 1 h / 45 °C

4.1: thionyl chloride / dichloromethane / 20 °C

4.2: 0 - 20 °C

4.3: 0 - 20 °C

With thionyl chloride; iron; ammonium chloride; triethylamine; trichlorophosphate; In ethanol; dichloromethane; isopropyl alcohol; acetonitrile;
DOI:10.1016/j.bmc.2014.01.035

Reference yield:

: 4651-81-4
Methyl 2-aminothiophene-3-carboxylate

: 1595285-90-7
(E)-N-(4-((3-chloro-4-fluorophenyl)amino)thieno[2,3-d]pyrimidin-6-yl)-4-(3-hydroxyazetidin-1-yl)but-2-enamide

Guidance literature:: Multi-step reaction with 6 steps

1.1: Microwave irradiation

2.1: sulfuric acid; nitric acid / 2 h / 90 °C

3.1: trichlorophosphate; triethylamine / acetonitrile / 3 h / 70 °C

4.1: isopropyl alcohol / 2 h / 20 - 80 °C

5.1: iron; ammonium chloride / ethanol / 1 h / 45 °C

6.1: thionyl chloride / dichloromethane / 20 °C

6.2: 0 - 20 °C

6.3: 0 - 20 °C

With thionyl chloride; sulfuric acid; nitric acid; iron; ammonium chloride; triethylamine; trichlorophosphate; In ethanol; dichloromethane; isopropyl alcohol; acetonitrile;
DOI:10.1016/j.bmc.2014.01.035