(S)-methyl 2-(2-(3-bromophenyl)-7-chloro-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)-2-(tert-butoxy)acetate

Base Information

• Chemical Name: (S)-methyl 2-(2-(3-bromophenyl)-7-chloro-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)-2-(tert-butoxy)acetate
• CAS No.: 1451007-00-3
• Molecular Formula: C₂₀H₂₁BrClN₃O₃
• Molecular Weight: 466.762
• Mol file: 1451007-00-3.mol

Synonyms:(S)-methyl 2-(2-(3-bromophenyl)-7-chloro-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)-2-(tert-butoxy)acetate

Chemical Property of (S)-methyl 2-(2-(3-bromophenyl)-7-chloro-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)-2-(tert-butoxy)acetate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-methyl 2-(2-(3-bromophenyl)-7-chloro-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)-2-(tert-butoxy)acetate

There total 6 articles about (S)-methyl 2-(2-(3-bromophenyl)-7-chloro-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)-2-(tert-butoxy)acetate 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:

methyl 2-(2-(3-bromophenyl)-7-hydroxy-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)acetate (1567213-35-7) → (S)-methyl 2-(2-(3-bromophenyl)-7-chloro-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)-2-(tert-butoxy)acetate (1451007-00-3)

Guidance literature:

Multi-step reaction with 4 steps

1.1: N,N-dimethyl-aniline; trichlorophosphate / 2.5 h / 120 °C

2.1: potassium hexamethylsilazane / tetrahydrofuran / 1 h / -78 °C

2.2: 2.16 h / -78 °C

2.3: 1 h / 20 °C

3.1: (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; benzo[1,3,2]dioxaborole / toluene / 2.66 h / -35 - -15 °C

3.2: 0.17 h

4.1: perchloric acid / dichloromethane / 3 h / 20 °C

With perchloric acid; potassium hexamethylsilazane; N,N-dimethyl-aniline; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; trichlorophosphate; benzo[1,3,2]dioxaborole; In tetrahydrofuran; dichloromethane; toluene;

Reference yield:

methyl 3-bromobenzoate (618-89-3) → (S)-methyl 2-(2-(3-bromophenyl)-7-chloro-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)-2-(tert-butoxy)acetate (1451007-00-3)

Guidance literature:

Multi-step reaction with 7 steps

1.1: sodium hydride / tetrahydrofuran / 4 h / 75 °C

2.1: hydrazine hydrate / ethanol / 16 h / Reflux

3.1: toluene-4-sulfonic acid / o-xylene / 3.5 h / 135 °C

4.1: N,N-dimethyl-aniline; trichlorophosphate / 2.5 h / 120 °C

5.1: potassium hexamethylsilazane / tetrahydrofuran / 1 h / -78 °C

5.2: 2.16 h / -78 °C

5.3: 1 h / 20 °C

6.1: (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; benzo[1,3,2]dioxaborole / toluene / 2.66 h / -35 - -15 °C

6.2: 0.17 h

7.1: perchloric acid / dichloromethane / 3 h / 20 °C

With perchloric acid; potassium hexamethylsilazane; sodium hydride; toluene-4-sulfonic acid; hydrazine hydrate; N,N-dimethyl-aniline; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; trichlorophosphate; benzo[1,3,2]dioxaborole; In tetrahydrofuran; ethanol; dichloromethane; o-xylene; toluene;

Reference yield:

methyl 2-(2-(3-bromophenyl)-7-chloro-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)acetate (1567213-38-0) → (S)-methyl 2-(2-(3-bromophenyl)-7-chloro-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)-2-(tert-butoxy)acetate (1451007-00-3)

Guidance literature:

Multi-step reaction with 3 steps

1.1: potassium hexamethylsilazane / tetrahydrofuran / 1 h / -78 °C

1.2: 2.16 h / -78 °C

1.3: 1 h / 20 °C

2.1: (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; benzo[1,3,2]dioxaborole / toluene / 2.66 h / -35 - -15 °C

2.2: 0.17 h

3.1: perchloric acid / dichloromethane / 3 h / 20 °C

With perchloric acid; potassium hexamethylsilazane; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; benzo[1,3,2]dioxaborole; In tetrahydrofuran; dichloromethane; toluene;

upstream raw materials:

methyl 2-(2-(3-bromophenyl)-7-hydroxy-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)acetate

methyl 2-(2-(3-bromophenyl)-7-chloro-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)acetate

methyl 2-(2-(3-bromophenyl)-7-chloro-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)-2-oxoacetate

methyl 3-bromobenzoate

Downstream raw materials:

(S)-2-(2-([1,1'-biphenyl]-3-yl)-7-((1R,5S)-8-azabicyclo[3.2.1]octan-8-yl)-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)-2-(tert-butoxy)acetic acid

C₃₃H₃₈N₄O₃

C₂₇H₃₃BrN₄O₃

(S)-methyl 2-(7-(4-(allyloxy)-4-methylpiperidin-1-yl)-2-(2’-(but-3-en-1-yl)[1,1‘-biphenyl]-3-yl)-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)-2-(tert-butoxy)acetate