3-(2,6-difluoro-3,5-dimethoxyphenyl)-1-ethyl-8-(morpholin-4-ylmethyl)-1,3,4,7-tetrahydro-2H-pyrrolo[3’,2’:5,6]pyrido[4,3-d]pyrimidin-2-one

Base Information

• Chemical Name: 3-(2,6-difluoro-3,5-dimethoxyphenyl)-1-ethyl-8-(morpholin-4-ylmethyl)-1,3,4,7-tetrahydro-2H-pyrrolo[3’,2’:5,6]pyrido[4,3-d]pyrimidin-2-one
• CAS No.: 1513857-77-6
• Molecular Formula: C₂₄H₂₇F₂N₅O₄
• Molecular Weight: 487.506
• Mol file: 1513857-77-6.mol

Synonyms:3-(2,6-difluoro-3,5-dimethoxyphenyl)-1-ethyl-8-(morpholin-4-ylmethyl)-1,3,4,7-tetrahydro-2H-pyrrolo[3’,2’:5,6]pyrido[4,3-d]pyrimidin-2-one

Chemical Property of 3-(2,6-difluoro-3,5-dimethoxyphenyl)-1-ethyl-8-(morpholin-4-ylmethyl)-1,3,4,7-tetrahydro-2H-pyrrolo[3’,2’:5,6]pyrido[4,3-d]pyrimidin-2-one

Chemical Property:

• Boiling Point: 697.6±55.0 °C(Predicted)
• Density: 1.44±0.1 g/cm3(Predicted)

Purity/Quality:

99% ^*data from raw suppliers

Pemigatinib >98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: Pemigatinib is a potent inhibitor of FGFRs for the treatment of cholangiocarcinoma.

Technology Process of 3-(2,6-difluoro-3,5-dimethoxyphenyl)-1-ethyl-8-(morpholin-4-ylmethyl)-1,3,4,7-tetrahydro-2H-pyrrolo[3’,2’:5,6]pyrido[4,3-d]pyrimidin-2-one

There total 31 articles about 3-(2,6-difluoro-3,5-dimethoxyphenyl)-1-ethyl-8-(morpholin-4-ylmethyl)-1,3,4,7-tetrahydro-2H-pyrrolo[3’,2’:5,6]pyrido[4,3-d]pyrimidin-2-one 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: 87.6%

3-(2,6-difluoro-3,5-dimethoxyphenyl)-1-ethyl-8-(morpholin-4-ylmethyl)-7-(phenylsulfonyl)-1,3,4,7-tetrahydro-2H-pyrrolo[3‘,2’: 5,6]pyrido[4,3-d]pyrimidin-2-one (1513860-02-0) → 3-(2,6-difluoro-3,5-dimethoxyphenyl)-1-ethyl-8-(morpholin-4-ylmethyl)-1,3,4,7-tetrahydro-2H-pyrrolo[3’,2’:5,6]pyrido[4,3-d]pyrimidin-2-one (1513857-77-6)

Guidance literature:

With sodium hydroxide; In 1,4-dioxane; water; at 75 ℃; for 18h;

Reference yield:

4-chloro-7-azaindole (55052-28-3) → 3-(2,6-difluoro-3,5-dimethoxyphenyl)-1-ethyl-8-(morpholin-4-ylmethyl)-1,3,4,7-tetrahydro-2H-pyrrolo[3’,2’:5,6]pyrido[4,3-d]pyrimidin-2-one (1513857-77-6)

Guidance literature:

Multi-step reaction with 11 steps

1.1: sodium hydride / mineral oil; tetrahydrofuran / 1 h / 0 - 20 °C / Inert atmosphere

1.2: 20 h / 25 °C

2.1: sec.-butyllithium / cyclohexane; tetrahydrofuran / 8 h / -75 - -60 °C / Inert atmosphere; Large scale

2.2: 2 h / -75 - -65 °C / Large scale

3.1: caesium carbonate / N,N-dimethyl-formamide / 0.33 h / 0 - 5 °C / Large scale

3.2: 1 h / 10 °C / Large scale

4.1: p-toluenesulfonic acid monohydrate / toluene / 9 h / 20 °C / Reflux; Large scale

5.1: lithium diisopropyl amide / ethylbenzene; tetrahydrofuran; n-heptane / 1 h / -70 °C / Inert atmosphere

5.2: 0.5 h

6.1: acetic acid / 0 - 18 °C

6.2: 0.5 h / 20 - 32 °C

7.1: hydrogenchloride / water; dichloromethane / 0.12 h / 20 °C

8.1: chloro-trimethyl-silane / N,N-dimethyl-formamide / 0.25 h / 20 - 23 °C

8.2: 4.5 h / 0 - 5 °C

9.1: methanesulfonic acid / acetonitrile / 24.58 h / 0 - 20 °C

10.1: lithium hexamethyldisilazane / tetrahydrofuran / 2 h / 20 °C

11.1: sodium hydroxide / water; 1,4-dioxane / 18 h / 75 °C

With hydrogenchloride; chloro-trimethyl-silane; methanesulfonic acid; p-toluenesulfonic acid monohydrate; sec.-butyllithium; sodium hydride; caesium carbonate; acetic acid; sodium hydroxide; lithium hexamethyldisilazane; lithium diisopropyl amide; In tetrahydrofuran; 1,4-dioxane; n-heptane; dichloromethane; cyclohexane; ethylbenzene; water; N,N-dimethyl-formamide; toluene; acetonitrile; mineral oil;

Reference yield:

methyl pentafluorobenzoate (36629-42-2) → 3-(2,6-difluoro-3,5-dimethoxyphenyl)-1-ethyl-8-(morpholin-4-ylmethyl)-1,3,4,7-tetrahydro-2H-pyrrolo[3’,2’:5,6]pyrido[4,3-d]pyrimidin-2-one (1513857-77-6)

Guidance literature:

Multi-step reaction with 8 steps

1.1: N-ethyl-N,N-diisopropylamine / 1-methyl-pyrrolidin-2-one / 4.5 h / 50 - 65 °C / Large scale

2.1: methanol / 21 h / 20 - 70 °C / Inert atmosphere; Large scale

3.1: sodium hydroxide / water; tert-butyl methyl ether / 0.5 h / 20 - 85 °C / Inert atmosphere; Large scale

4.1: ammonium formate; palladium on activated charcoal; acetic acid / ethanol / 50 °C / Large scale

4.2: 3 h / Reflux; Large scale

5.1: chloro-trimethyl-silane / N,N-dimethyl-formamide / 0.25 h / 20 - 23 °C

5.2: 4.5 h / 0 - 5 °C

6.1: methanesulfonic acid / acetonitrile / 24.58 h / 0 - 20 °C

7.1: lithium hexamethyldisilazane / tetrahydrofuran / 2 h / 20 °C

8.1: sodium hydroxide / water; 1,4-dioxane / 18 h / 75 °C

With chloro-trimethyl-silane; methanesulfonic acid; palladium on activated charcoal; ammonium formate; acetic acid; N-ethyl-N,N-diisopropylamine; sodium hydroxide; lithium hexamethyldisilazane; In tetrahydrofuran; 1,4-dioxane; 1-methyl-pyrrolidin-2-one; methanol; ethanol; tert-butyl methyl ether; water; N,N-dimethyl-formamide; acetonitrile;

upstream raw materials:

3-(2,6-difluoro-3,5-dimethoxyphenyl)-1-ethyl-1,3,4,7-tetrahydro-2H-pyrrolo[3′,2’:5,6] pyrido[4,3-d]-pyrimidin-2-one

4-chloro-1H-pyrrolo[2,3-b]pyridine-5-carbaldehyde

4-(ethylamino)-1H-pyrrolo[2,3-b]pyridine-5-carbaldehyde

5-{[(2,6-difluoro-3,5-dimethoxyphenyl)amino]methyl}-N-ethyl-1H-pyrrolo[2,3-b]pyridin-4-amine

Refernces

• 1、 -. "DERIVATIVES OF AN FGFR INHIBITOR". . . Retrieved 2021/06/11.
• 2、 -. "SOLID FORMS OF AN FGFR INHIBITOR AND PROCESSES FOR PREPARING THE SAME". . . Retrieved 2019/11/19.