4-[7-cyclopentylamino-3-(2-cyclopentylamino-pyrimidin-4-yl)-pyrazolo[1,5-a]pyridin-2-yl]-phenol

Base Information

• Chemical Name: 4-[7-cyclopentylamino-3-(2-cyclopentylamino-pyrimidin-4-yl)-pyrazolo[1,5-a]pyridin-2-yl]-phenol
• CAS No.: 460078-26-6
• Molecular Formula: C₂₇H₃₀N₆O
• Molecular Weight: 454.575

Synonyms:4-[7-cyclopentylamino-3-(2-cyclopentylamino-pyrimidin-4-yl)-pyrazolo[1,5-a]pyridin-2-yl]-phenol

Chemical Property of 4-[7-cyclopentylamino-3-(2-cyclopentylamino-pyrimidin-4-yl)-pyrazolo[1,5-a]pyridin-2-yl]-phenol

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Technology Process of 4-[7-cyclopentylamino-3-(2-cyclopentylamino-pyrimidin-4-yl)-pyrazolo[1,5-a]pyridin-2-yl]-phenol

There total 9 articles about 4-[7-cyclopentylamino-3-(2-cyclopentylamino-pyrimidin-4-yl)-pyrazolo[1,5-a]pyridin-2-yl]-phenol 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%

cyclopentyl-[3-(2-cyclopentylamino-pyrimidin-4-yl)-2-(4-methoxy-phenyl)-pyrazolo[1,5-a]pyridin-7-yl]-amine (460078-20-0) → 4-[7-cyclopentylamino-3-(2-cyclopentylamino-pyrimidin-4-yl)-pyrazolo[1,5-a]pyridin-2-yl]-phenol (460078-26-6)

Guidance literature:

With boron tribromide; In dichloromethane; at 20 ℃; for 15h;

DOI:10.1016/j.bmc.2005.05.043

Reference yield:

2-(6-chloro-2-pyridinyl)-1-(4-methoxyphenyl)ethanone (437384-15-1) → 4-[7-cyclopentylamino-3-(2-cyclopentylamino-pyrimidin-4-yl)-pyrazolo[1,5-a]pyridin-2-yl]-phenol (460078-26-6)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 97 percent / hydroxylamine hydrochloride; NaOH / methanol; H₂O / Heating

2.1: frifluoroacetic anhydride; triethylamine / 1,2-dimethoxy-ethane / 0 - 20 °C

2.2: 52 percent / iron(II) chloride / 1,2-dimethoxy-ethane / 8 h / Heating

3.1: 65 percent / BF₃*Et₂O / toluene / Heating

4.1: 97 percent / rac-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl; cesium carbonate / palladium(II) acetate / toluene / 100 °C

5.1: 93 percent / 120 h / Heating

6.1: 73 percent / K₂CO₃ / ethanol / Heating

7.1: 71 percent / boron tribromide / CH₂Cl₂ / 15 h / 20 °C

With sodium hydroxide; boron trifluoride diethyl etherate; hydroxylamine hydrochloride; boron tribromide; potassium carbonate; caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; triethylamine; trifluoroacetic anhydride; palladium diacetate; In methanol; 1,2-dimethoxyethane; ethanol; dichloromethane; water; toluene; 4.1: Buchwald-Hartwig amination;

DOI:10.1016/j.bmc.2005.05.043

Reference yield:

7-chloro-2-(4-methoxyphenyl)pyrazolo[1,5-a]pyridine (437384-17-3) → 4-[7-cyclopentylamino-3-(2-cyclopentylamino-pyrimidin-4-yl)-pyrazolo[1,5-a]pyridin-2-yl]-phenol (460078-26-6)

Guidance literature:

Multi-step reaction with 5 steps

1: 65 percent / BF₃*Et₂O / toluene / Heating

2: 97 percent / rac-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl; cesium carbonate / palladium(II) acetate / toluene / 100 °C

3: 93 percent / 120 h / Heating

4: 73 percent / K₂CO₃ / ethanol / Heating

5: 71 percent / boron tribromide / CH₂Cl₂ / 15 h / 20 °C

With boron trifluoride diethyl etherate; boron tribromide; potassium carbonate; caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; palladium diacetate; In ethanol; dichloromethane; toluene; 2: Buchwald-Hartwig amination;

DOI:10.1016/j.bmc.2005.05.043

upstream raw materials:

cyclopentyl-[3-(2-cyclopentylamino-pyrimidin-4-yl)-2-(4-methoxy-phenyl)-pyrazolo[1,5-a]pyridin-7-yl]-amine

7-chloro-2-(4-methoxyphenyl)pyrazolo[1,5-a]pyridine

2-(6-chloro-2-pyridinyl)-1-(4-methoxyphenyl)ethanone

2-(6-chloro-2-pyridinyl)-1-(4-methoxyphenyl)ethanone oxime

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