10-[2-(acetoxymethyl)-3-[1-methyl-6-oxo-5-(pyrimidin-4-ylamino)-1,6-dihydropyridin-3-yl]phenyl]-4,4-dimethyl-1,10-diazatricyclo[6.4.0.0(2,6)]dodeca-⁽⁶⁾,7-dien-9-one

Base Information

• Chemical Name: 10-[2-(acetoxymethyl)-3-[1-methyl-6-oxo-5-(pyrimidin-4-ylamino)-1,6-dihydropyridin-3-yl]phenyl]-4,4-dimethyl-1,10-diazatricyclo[6.4.0.0(2,6)]dodeca-⁽⁶⁾,7-dien-9-one
• CAS No.: 1346674-25-6
• Molecular Formula: C₃₁H₃₂N₆O₄
• Molecular Weight: 552.633

Synonyms:10-[2-(acetoxymethyl)-3-[1-methyl-6-oxo-5-(pyrimidin-4-ylamino)-1,6-dihydropyridin-3-yl]phenyl]-4,4-dimethyl-1,10-diazatricyclo[6.4.0.0(2,6)]dodeca-⁽⁶⁾,7-dien-9-one

Chemical Property of 10-[2-(acetoxymethyl)-3-[1-methyl-6-oxo-5-(pyrimidin-4-ylamino)-1,6-dihydropyridin-3-yl]phenyl]-4,4-dimethyl-1,10-diazatricyclo[6.4.0.0(2,6)]dodeca-⁽⁶⁾,7-dien-9-one

Chemical Property:

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Technology Process of 10-[2-(acetoxymethyl)-3-[1-methyl-6-oxo-5-(pyrimidin-4-ylamino)-1,6-dihydropyridin-3-yl]phenyl]-4,4-dimethyl-1,10-diazatricyclo[6.4.0.0(2,6)]dodeca-⁽⁶⁾,7-dien-9-one

There total 13 articles about 10-[2-(acetoxymethyl)-3-[1-methyl-6-oxo-5-(pyrimidin-4-ylamino)-1,6-dihydropyridin-3-yl]phenyl]-4,4-dimethyl-1,10-diazatricyclo[6.4.0.0(2,6)]dodeca-⁽⁶⁾,7-dien-9-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: 53.0%

1-methyl-3-(pyrimidin-4-ylamino)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2(1H)-one (1346672-60-3) + 2-bromo-6-(7,7-dimethyl-1-oxo-3,4,7,8-tetrahydro-1H-cyclopenta[4,5]pyrrolo[1,2-a]pyrazin-2(6H)-yl)benzyl acetate (1346674-24-5) → 10-[2-(acetoxymethyl)-3-[1-methyl-6-oxo-5-(pyrimidin-4-ylamino)-1,6-dihydropyridin-3-yl]phenyl]-4,4-dimethyl-1,10-diazatricyclo[6.4.0.0(2,6)]dodeca-(6),7-dien-9-one (1346674-25-6)

Guidance literature:

With sodium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In 1,2-dimethoxyethane; water; at 130 ℃; for 0.416667h; Inert atmosphere; microwave irradiation;

Reference yield:

2,6-dibromotoluene (69321-60-4) → 10-[2-(acetoxymethyl)-3-[1-methyl-6-oxo-5-(pyrimidin-4-ylamino)-1,6-dihydropyridin-3-yl]phenyl]-4,4-dimethyl-1,10-diazatricyclo[6.4.0.0(2,6)]dodeca-(6),7-dien-9-one (1346674-25-6)

Guidance literature:

Multi-step reaction with 4 steps

1: N-Bromosuccinimide / 2,2'-azobis(isobutyronitrile) / tetrachloromethane / 14 h / 80 °C / Inert atmosphere

2: N,N-dimethyl-formamide / 14 h / 20 °C / Inert atmosphere

3: caesium carbonate / N,N,N,N,-tetramethylethylenediamine; copper(l) iodide / 1,2-dimethoxyethane / 3 h / 150 °C / microwave irradiation

4: sodium carbonate / tetrakis(triphenylphosphine) palladium⁽⁰⁾ / 1,2-dimethoxyethane; water / 0.42 h / 130 °C / Inert atmosphere; microwave irradiation

With N-Bromosuccinimide; sodium carbonate; caesium carbonate; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; 2,2'-azobis(isobutyronitrile); N,N,N,N,-tetramethylethylenediamine; In tetrachloromethane; 1,2-dimethoxyethane; water; N,N-dimethyl-formamide;

Reference yield:

3,3-dimethylcyclopentanone (20500-49-6) → 10-[2-(acetoxymethyl)-3-[1-methyl-6-oxo-5-(pyrimidin-4-ylamino)-1,6-dihydropyridin-3-yl]phenyl]-4,4-dimethyl-1,10-diazatricyclo[6.4.0.0(2,6)]dodeca-(6),7-dien-9-one (1346674-25-6)

Guidance literature:

Multi-step reaction with 8 steps

1.1: trichlorophosphate / dichloromethane / 1.5 h / 0 - 20 °C / Inert atmosphere

1.2: 19 h / Reflux

1.3: 0.75 h / Cooling with ice

2.1: benzene / 14 h / Inert atmosphere

3.1: sodium azide / dimethyl sulfoxide / 8 h / 75 °C / Inert atmosphere

4.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 1.5 h / 20 °C / Inert atmosphere

4.2: 14 h

5.1: hydrogenchloride; hydrogen / palladium 10% on activated carbon / ethyl acetate; ethanol; water / 6 h / 2585.81 Torr / Inert atmosphere

6.1: sodium ethanolate / ethanol / 55 °C / Inert atmosphere

7.1: caesium carbonate / N,N,N,N,-tetramethylethylenediamine; copper(l) iodide / 1,2-dimethoxyethane / 3 h / 150 °C / microwave irradiation

8.1: sodium carbonate / tetrakis(triphenylphosphine) palladium⁽⁰⁾ / 1,2-dimethoxyethane; water / 0.42 h / 130 °C / Inert atmosphere; microwave irradiation

With hydrogenchloride; sodium azide; hydrogen; sodium ethanolate; sodium hydride; sodium carbonate; caesium carbonate; trichlorophosphate; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; N,N,N,N,-tetramethylethylenediamine; palladium 10% on activated carbon; In 1,2-dimethoxyethane; ethanol; dichloromethane; water; dimethyl sulfoxide; ethyl acetate; N,N-dimethyl-formamide; mineral oil; benzene;

upstream raw materials:

2,6-dibromotoluene

3,3-dimethylcyclopentanone

3,5-dibromo-1-methyl-1H-pyridin-2-one

3-Methyl-2-cyclopenten-1-one

Downstream raw materials:

10-[2-(hydroxymethyl)-3-[1-methyl-6-oxo-5-(pyrimidin-4-ylamino)-1,6-dihydropyridin-3-yl]phenyl]-4,4-dimethyl-1,10-diazatricyclo[6.4.0.0(2,6)]dodeca-2⁽⁶⁾,7-dien-9-one

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