4-(7-hydroxy-2-methyl-3-(2-methyl-3-(trifluoromethyl)benzyl)pyrazolo[1,5-a]pyrimidin-5-yl)morpholin-3-one

Base Information

• Chemical Name: 4-(7-hydroxy-2-methyl-3-(2-methyl-3-(trifluoromethyl)benzyl)pyrazolo[1,5-a]pyrimidin-5-yl)morpholin-3-one
• CAS No.: 1420468-55-8
• Molecular Formula: C₂₀H₁₉F₃N₄O₃
• Molecular Weight: 420.391

Synonyms:4-(7-hydroxy-2-methyl-3-(2-methyl-3-(trifluoromethyl)benzyl)pyrazolo[1,5-a]pyrimidin-5-yl)morpholin-3-one

Chemical Property of 4-(7-hydroxy-2-methyl-3-(2-methyl-3-(trifluoromethyl)benzyl)pyrazolo[1,5-a]pyrimidin-5-yl)morpholin-3-one

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Technology Process of 4-(7-hydroxy-2-methyl-3-(2-methyl-3-(trifluoromethyl)benzyl)pyrazolo[1,5-a]pyrimidin-5-yl)morpholin-3-one

There total 8 articles about 4-(7-hydroxy-2-methyl-3-(2-methyl-3-(trifluoromethyl)benzyl)pyrazolo[1,5-a]pyrimidin-5-yl)morpholin-3-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: 2.0%

morpholine-3-one (109-11-5) + 5-chloro-2-methyl-3-{[2-methyl-3-(trifluoromethyl)phenyl]methyl}pyrazolo[1,5-a]pyrimidin-7(4H)-one (1420468-34-3) → 4-(7-hydroxy-2-methyl-3-(2-methyl-3-(trifluoromethyl)benzyl)pyrazolo[1,5-a]pyrimidin-5-yl)morpholin-3-one (1420468-55-8)

Guidance literature:

With 2-di-tertbutylphosphino-3,4,5,6-tetramethyl-2',4',6'-triisopropyl-1,1'-biphenyl; potassium phosphate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; In tert-butyl alcohol; at 110 ℃; for 24h; Inert atmosphere;

DOI:10.1021/ml300330m

Reference yield:

2-{[2-methyl-3-(trifluoromethyl)phenyl]methyl}-3-oxobutanenitrile (1420468-30-9) → 4-(7-hydroxy-2-methyl-3-(2-methyl-3-(trifluoromethyl)benzyl)pyrazolo[1,5-a]pyrimidin-5-yl)morpholin-3-one (1420468-55-8)

Guidance literature:

Multi-step reaction with 5 steps

1: hydrazine hydrate / ethanol / 20 - 100 °C / Inert atmosphere

2: sodium methylate / methanol / 20 - 80 °C / Inert atmosphere

3: N,N-diethylaniline; trichlorophosphate / 3.25 h / 0 - 80 °C / Inert atmosphere

4: sodium hydroxide / tetrahydrofuran / 3 h / 50 °C

5: 2-di-tertbutylphosphino-3,4,5,6-tetramethyl-2',4',6'-triisopropyl-1,1'-biphenyl; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; potassium phosphate / tert-butyl alcohol / 24 h / 110 °C / Inert atmosphere

With 2-di-tertbutylphosphino-3,4,5,6-tetramethyl-2',4',6'-triisopropyl-1,1'-biphenyl; potassium phosphate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; sodium methylate; hydrazine hydrate; N,N-diethylaniline; sodium hydroxide; trichlorophosphate; In tetrahydrofuran; methanol; ethanol; tert-butyl alcohol;

DOI:10.1021/ml300330m

Reference yield:

5,7-dichloro-2-methyl-3-{[2-methyl-3-(trifluoromethyl)phenyl]methyl}pyrazolo[1,5-a]pyrimidine (1420468-33-2) → 4-(7-hydroxy-2-methyl-3-(2-methyl-3-(trifluoromethyl)benzyl)pyrazolo[1,5-a]pyrimidin-5-yl)morpholin-3-one (1420468-55-8)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium hydroxide / tetrahydrofuran / 3 h / 50 °C

2: 2-di-tertbutylphosphino-3,4,5,6-tetramethyl-2',4',6'-triisopropyl-1,1'-biphenyl; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; potassium phosphate / tert-butyl alcohol / 24 h / 110 °C / Inert atmosphere

With 2-di-tertbutylphosphino-3,4,5,6-tetramethyl-2',4',6'-triisopropyl-1,1'-biphenyl; potassium phosphate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; sodium hydroxide; In tetrahydrofuran; tert-butyl alcohol;

DOI:10.1021/ml300330m

upstream raw materials:

1-(bromomethyl)-2-methyl-3-(trifluoromethyl)benzene

2-{[2-methyl-3-(trifluoromethyl)phenyl]methyl}-3-oxobutanenitrile

5-methyl-4-[[2-methyl-3-(trifluoromethyl)phenyl]methyl]-1H-pyrazol-3-amine

2-methyl-3-{[2-methyl-3-(trifluoromethyl)phenyl]methyl}pyrazolo[1,5-a]pyrimidine-5,7(4H,6H)-dione

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