3-(1,3-dimethyl-2,4-dioxo-10-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,4,7,8-hexahydropyrimido[4,5-a]indolizin-5-yl)benzonitrile

Base Information

• Chemical Name: 3-(1,3-dimethyl-2,4-dioxo-10-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,4,7,8-hexahydropyrimido[4,5-a]indolizin-5-yl)benzonitrile
• CAS No.: 1614251-46-5
• Molecular Formula: C₂₅H₂₇BN₄O₄
• Molecular Weight: 458.325
• Mol file: 1614251-46-5.mol

Synonyms:3-(1,3-dimethyl-2,4-dioxo-10-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,4,7,8-hexahydropyrimido[4,5-a]indolizin-5-yl)benzonitrile

Chemical Property of 3-(1,3-dimethyl-2,4-dioxo-10-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,4,7,8-hexahydropyrimido[4,5-a]indolizin-5-yl)benzonitrile

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-(1,3-dimethyl-2,4-dioxo-10-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,4,7,8-hexahydropyrimido[4,5-a]indolizin-5-yl)benzonitrile

There total 10 articles about 3-(1,3-dimethyl-2,4-dioxo-10-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,4,7,8-hexahydropyrimido[4,5-a]indolizin-5-yl)benzonitrile 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:

5-(3-cyanophenyl)-1,3-dimethyl-2,4-dioxo-1,2,3,4,7,8-hexahydropyrimido[4,5-a]indolizin-10-yl trifluoromethanesulfonate (1614251-45-4) + bis(pinacol)diborane (73183-34-3) → 3-(1,3-dimethyl-2,4-dioxo-10-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,4,7,8-hexahydropyrimido[4,5-a]indolizin-5-yl)benzonitrile (1614251-46-5)

Guidance literature:

With bis-triphenylphosphine-palladium(II) chloride; potassium phenolate; triphenylphosphine; In toluene; at 60 ℃; for 3h; Inert atmosphere;

Reference yield:

1,3-dimethyl-2,4-dioxo-6-((2-(trimethylsilyl)ethoxy)methyl)-2,3,4,6-tetrahydro-1H-pyrrolo[3,4-d]pyrimidin-5-ylboronic acid (1613623-81-6) → 3-(1,3-dimethyl-2,4-dioxo-10-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,4,7,8-hexahydropyrimido[4,5-a]indolizin-5-yl)benzonitrile (1614251-46-5)

Guidance literature:

Multi-step reaction with 7 steps

1.1: potassium carbonate / acetic acid butyl ester; water / 1.5 h / 80 °C

2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 60 °C

3.1: caesium carbonate / N,N-dimethyl-formamide / 2 h / 80 °C

4.1: lithium hydroxide; water / tetrahydrofuran / 4 h / 20 °C

4.2: pH 1

5.1: 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide / N,N-dimethyl-formamide / 12 h / 100 °C

6.1: 2,6-dimethylpyridine / dichloromethane / 2 h / Cooling with ice

7.1: triphenylphosphine; bis-triphenylphosphine-palladium(II) chloride; potassium phenolate / toluene / 3 h / 60 °C / Inert atmosphere

With 2,6-dimethylpyridine; bis-triphenylphosphine-palladium(II) chloride; potassium phenolate; tetrabutyl ammonium fluoride; water; potassium carbonate; caesium carbonate; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; triphenylphosphine; lithium hydroxide; In tetrahydrofuran; dichloromethane; acetic acid butyl ester; water; N,N-dimethyl-formamide; toluene;

Reference yield:

methyl 4-(5-(3-cyanophenyl)-1,3-dimethyl-2,4-dioxo-3,4-dihydro-1H-pyrrolo[3,4-d]pyrimidin-6(2H)-yl)butanoate (1614251-42-1) → 3-(1,3-dimethyl-2,4-dioxo-10-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,4,7,8-hexahydropyrimido[4,5-a]indolizin-5-yl)benzonitrile (1614251-46-5)

Guidance literature:

Multi-step reaction with 4 steps

1.1: lithium hydroxide; water / tetrahydrofuran / 4 h / 20 °C

1.2: pH 1

2.1: 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide / N,N-dimethyl-formamide / 12 h / 100 °C

3.1: 2,6-dimethylpyridine / dichloromethane / 2 h / Cooling with ice

4.1: triphenylphosphine; bis-triphenylphosphine-palladium(II) chloride; potassium phenolate / toluene / 3 h / 60 °C / Inert atmosphere

With 2,6-dimethylpyridine; bis-triphenylphosphine-palladium(II) chloride; potassium phenolate; water; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; triphenylphosphine; lithium hydroxide; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; toluene;

upstream raw materials:

1,3-dimethyl-2,4-dioxo-6-((2-(trimethylsilyl)ethoxy)methyl)-2,3,4,6-tetrahydro-1H-pyrrolo[3,4-d]pyrimidin-5-ylboronic acid

3-(1,3-dimethyl-2,4-dioxo-6-((2-(trimethylsilyl)ethoxy)methyl)-2,3,4,6-tetrahydro-1H-pyrrolo[3,4-d]pyrimidin-5-yl)benzonitrile

3-(1,3-dimethyl-2,4-dioxo-2,3,4,6-tetrahydro-1H-pyrrolo[3,4-d]pyrimidin-5-yl)benzonitrile

methyl 4-(5-(3-cyanophenyl)-1,3-dimethyl-2,4-dioxo-3,4-dihydro-1H-pyrrolo[3,4-d]pyrimidin-6(2H)-yl)butanoate

Downstream raw materials:

3-(1,3-dimethyl-10-(4-methylthiazol-2-yl)-2,4-dioxo-1,2,3,4,7,8,9,10-octahydropyrimido[4,5-a]indolizin-5-yl)benzonitrile

3-(1,3-dimethyl-10-(4-methylthiazol-2-yl)-2,4-dioxo-1,2,3,4,7,8-hexahydropyrimido[4,5-a]indolizin-5-yl)benzonitrile