(4aR,7aS)-6-(5-fluoro-4-methoxy-6-methylpyrimidin-2-yl)-2-imino-3-methyl-7a-(2,3,4,6-tetrafluorophenyl)hexahydro-1H-pyrrolo[3,4-d]pyrimidin-4(4aH)-one

Base Information

• Chemical Name: (4aR,7aS)-6-(5-fluoro-4-methoxy-6-methylpyrimidin-2-yl)-2-imino-3-methyl-7a-(2,3,4,6-tetrafluorophenyl)hexahydro-1H-pyrrolo[3,4-d]pyrimidin-4(4aH)-one
• CAS No.: 1192494-53-3
• Molecular Formula: C₁₉H₁₇F₅N₆O₂
• Molecular Weight: 456.375
• Mol file: 1192494-53-3.mol

Synonyms:(4aR,7aS)-6-(5-fluoro-4-methoxy-6-methylpyrimidin-2-yl)-2-imino-3-methyl-7a-(2,3,4,6-tetrafluorophenyl)hexahydro-1H-pyrrolo[3,4-d]pyrimidin-4(4aH)-one

Chemical Property of (4aR,7aS)-6-(5-fluoro-4-methoxy-6-methylpyrimidin-2-yl)-2-imino-3-methyl-7a-(2,3,4,6-tetrafluorophenyl)hexahydro-1H-pyrrolo[3,4-d]pyrimidin-4(4aH)-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4aR,7aS)-6-(5-fluoro-4-methoxy-6-methylpyrimidin-2-yl)-2-imino-3-methyl-7a-(2,3,4,6-tetrafluorophenyl)hexahydro-1H-pyrrolo[3,4-d]pyrimidin-4(4aH)-one

There total 27 articles about (4aR,7aS)-6-(5-fluoro-4-methoxy-6-methylpyrimidin-2-yl)-2-imino-3-methyl-7a-(2,3,4,6-tetrafluorophenyl)hexahydro-1H-pyrrolo[3,4-d]pyrimidin-4(4aH)-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: 80.0%

C24H25F5N6O4 → (4aR,7aS)-6-(5-fluoro-4-methoxy-6-methylpyrimidin-2-yl)-2-imino-3-methyl-7a-(2,3,4,6-tetrafluorophenyl)hexahydro-1H-pyrrolo[3,4-d]pyrimidin-4(4aH)-one (1192494-53-3)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; for 0.333333h;

DOI:10.1002/ejoc.202101056

Reference yield:

(4aR,7aS)-benzyl 2-((tert-butoxycarbonyl)imino)-3-methyl-4-oxo-7a-(2,3,4,6-tetrafluorophenyl)hexahydro-1H-pyrrolo[3,4-d]pyrimidine-6(2H)-carboxylate → (4aR,7aS)-6-(5-fluoro-4-methoxy-6-methylpyrimidin-2-yl)-2-imino-3-methyl-7a-(2,3,4,6-tetrafluorophenyl)hexahydro-1H-pyrrolo[3,4-d]pyrimidin-4(4aH)-one (1192494-53-3)

Guidance literature:

Multi-step reaction with 3 steps

1: hydrogen; 20% palladium hydroxide-activated charcoal / methanol / 5 h / 20 °C

2: johnphos; sodium t-butanolate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / toluene / 4 h / 65 °C / Inert atmosphere; Sealed tube

3: trifluoroacetic acid / dichloromethane / 3 h / 20 °C

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; 20% palladium hydroxide-activated charcoal; hydrogen; trifluoroacetic acid; johnphos; sodium t-butanolate; In methanol; dichloromethane; toluene;

DOI:10.1021/acs.jmedchem.5b01995

Reference yield:

2-(2,3,4,6-tetrafluorophenyl)acetonitrile (53001-75-5) → (4aR,7aS)-6-(5-fluoro-4-methoxy-6-methylpyrimidin-2-yl)-2-imino-3-methyl-7a-(2,3,4,6-tetrafluorophenyl)hexahydro-1H-pyrrolo[3,4-d]pyrimidin-4(4aH)-one (1192494-53-3)

Guidance literature:

Multi-step reaction with 14 steps

1.1: potassium carbonate / methanol / 0 - 20 °C

2.1: sulfuric acid; formic acid / 100 °C

3.1: sulfuric acid / 100 °C / Reflux

4.1: trifluoroacetic acid / tetrahydrofuran / 0 - 20 °C

4.2: Reflux

5.1: acetic anhydride / 90 °C

5.2: -78 - 20 °C

6.1: palladium(II) hydroxide / methanol / 20 °C

7.1: triethylamine / tetrahydrofuran / 0 - 20 °C

8.1: triethylamine; diphenyl phosphoryl azide / toluene / 3 h / 75 °C

8.2: 2 h / 110 °C

9.1: hydrogenchloride / 1,4-dioxane / 20 h / 20 °C

10.1: N-ethyl-N,N-diisopropylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 156 h / 20 °C

11.1: Chiralpak AD column / hexane; isopropyl alcohol / Resolution of racemate

12.1: hydrogen; 20% palladium hydroxide-activated charcoal / methanol / 5 h / 20 °C

13.1: johnphos; sodium t-butanolate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / toluene / 4 h / 65 °C / Inert atmosphere; Sealed tube

14.1: trifluoroacetic acid / dichloromethane / 3 h / 20 °C

With hydrogenchloride; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; formic acid; sulfuric acid; diphenyl phosphoryl azide; 20% palladium hydroxide-activated charcoal; hydrogen; palladium(II) hydroxide; acetic anhydride; potassium carbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; johnphos; sodium t-butanolate; In tetrahydrofuran; 1,4-dioxane; methanol; hexane; dichloromethane; N,N-dimethyl-formamide; isopropyl alcohol; toluene; 8.2: |Curtius Rearrangement;

DOI:10.1021/acs.jmedchem.5b01995

upstream raw materials:

2,4-dichloro-5-fluoro-6-methyl-pyrimidine

2-chloro-5-fluoro-4-methoxy-6-methyl-pyrimidine

2-(bromomethyl)-1,3,4,5-tetrafluorobenzene

2-(2,3,4,6-tetrafluorophenyl)acetonitrile