(2S)-methyl 2-(7-(4-allyl-5-chloro-3,4-dihydro-2H-benzo[b][1,4]oxazin-6-yl)-2-(2‘-hydroxy-[1,1‘-biphenyl]-3-yl)-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)-2-(tert-butoxy)acetate

Base Information

• Chemical Name: (2S)-methyl 2-(7-(4-allyl-5-chloro-3,4-dihydro-2H-benzo[b][1,4]oxazin-6-yl)-2-(2‘-hydroxy-[1,1‘-biphenyl]-3-yl)-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)-2-(tert-butoxy)acetate
• CAS No.: 1567213-97-1
• Molecular Formula: C₃₇H₃₇ClN₄O₅
• Molecular Weight: 653.178
• Mol file: 1567213-97-1.mol

Synonyms:(2S)-methyl 2-(7-(4-allyl-5-chloro-3,4-dihydro-2H-benzo[b][1,4]oxazin-6-yl)-2-(2‘-hydroxy-[1,1‘-biphenyl]-3-yl)-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)-2-(tert-butoxy)acetate

Chemical Property of (2S)-methyl 2-(7-(4-allyl-5-chloro-3,4-dihydro-2H-benzo[b][1,4]oxazin-6-yl)-2-(2‘-hydroxy-[1,1‘-biphenyl]-3-yl)-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 (2S)-methyl 2-(7-(4-allyl-5-chloro-3,4-dihydro-2H-benzo[b][1,4]oxazin-6-yl)-2-(2‘-hydroxy-[1,1‘-biphenyl]-3-yl)-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)-2-(tert-butoxy)acetate

There total 13 articles about (2S)-methyl 2-(7-(4-allyl-5-chloro-3,4-dihydro-2H-benzo[b][1,4]oxazin-6-yl)-2-(2‘-hydroxy-[1,1‘-biphenyl]-3-yl)-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:

(2S)-methyl 2-(7-(4-allyl-5-chloro-3,4-dihydro-2H-benzo[b][1,4]oxazin-6-yl)-2-(3-bromophenyl)-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)-2-(tert-butoxy)acetate (1567213-59-5) + 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (269409-97-4) → (2S)-methyl 2-(7-(4-allyl-5-chloro-3,4-dihydro-2H-benzo[b][1,4]oxazin-6-yl)-2-(2‘-hydroxy-[1,1‘-biphenyl]-3-yl)-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)-2-(tert-butoxy)acetate (1567213-97-1)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate; In 1,4-dioxane; water; at 90 ℃; for 1.5h; Microwave irradiation; Inert atmosphere;

Reference yield:

methyl 2-(2-(3-bromophenyl)-7-hydroxy-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)acetate (1567213-35-7) → (2S)-methyl 2-(7-(4-allyl-5-chloro-3,4-dihydro-2H-benzo[b][1,4]oxazin-6-yl)-2-(2‘-hydroxy-[1,1‘-biphenyl]-3-yl)-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)-2-(tert-butoxy)acetate (1567213-97-1)

Guidance literature:

Multi-step reaction with 8 steps

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

2.1: sodium iodide / acetonitrile / 5 h / 80 °C

3.1: potassium hexamethylsilazane / tetrahydrofuran / 0.58 h / -78 °C

3.2: 0.5 h / -78 °C

4.1: Dess-Martin periodane / dichloromethane / 1 h / 20 °C

5.1: (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; benzo[1,3,2]dioxaborole / toluene / 2.58 h / -35 - -15 °C

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

7.1: sodium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / N,N-dimethyl-formamide / 16 h / 90 °C

8.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate / water; 1,4-dioxane / 1.5 h / 90 °C / Microwave irradiation; Inert atmosphere

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; perchloric acid; potassium hexamethylsilazane; sodium carbonate; potassium carbonate; Dess-Martin periodane; N,N-dimethyl-aniline; sodium iodide; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; trichlorophosphate; benzo[1,3,2]dioxaborole; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile; 3.1: |Davis' Oxaziridine Oxidations / 3.2: |Davis' Oxaziridine Oxidations / 4.1: |Dess-Martin Oxidation / 7.1: |Suzuki Coupling;

Reference yield:

methyl 2-(2-(3-bromophenyl)-7-chloro-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)acetate (1567213-38-0) → (2S)-methyl 2-(7-(4-allyl-5-chloro-3,4-dihydro-2H-benzo[b][1,4]oxazin-6-yl)-2-(2‘-hydroxy-[1,1‘-biphenyl]-3-yl)-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)-2-(tert-butoxy)acetate (1567213-97-1)

Guidance literature:

Multi-step reaction with 7 steps

1.1: sodium iodide / acetonitrile / 5 h / 80 °C

2.1: potassium hexamethylsilazane / tetrahydrofuran / 0.58 h / -78 °C

2.2: 0.5 h / -78 °C

3.1: Dess-Martin periodane / dichloromethane / 1 h / 20 °C

4.1: (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; benzo[1,3,2]dioxaborole / toluene / 2.58 h / -35 - -15 °C

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

6.1: sodium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / N,N-dimethyl-formamide / 16 h / 90 °C

7.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate / water; 1,4-dioxane / 1.5 h / 90 °C / Microwave irradiation; Inert atmosphere

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; perchloric acid; potassium hexamethylsilazane; sodium carbonate; potassium carbonate; Dess-Martin periodane; sodium iodide; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; benzo[1,3,2]dioxaborole; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile; 2.1: |Davis' Oxaziridine Oxidations / 2.2: |Davis' Oxaziridine Oxidations / 3.1: |Dess-Martin Oxidation / 6.1: |Suzuki Coupling;

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

5-chloro-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine

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

Downstream raw materials:

(2S)-methyl 2-(7-(4-allyl-5-chloro-3,4-dihydro-2H-benzo[b][1,4]oxazin-6-yl)-5-methyl-2-(2’-(pent-4-en-1-yloxy)-[1,1‘-biphenyl]-3-yl)pyrazolo[1,5-a]pyrimidin-6-yl)-2-(tert-butoxy)acetate