Technology Process of (4aS,5S,7aS)-7a-(2,4-difluoro-5-(pyrimidin-5-yl)phenyl)-5-(fluoromethyl)-4a,5,7,7a-tetrahydro-4H-furo[3,4-d][1,3]thiazin-2-amine
There total 13 articles about (4aS,5S,7aS)-7a-(2,4-difluoro-5-(pyrimidin-5-yl)phenyl)-5-(fluoromethyl)-4a,5,7,7a-tetrahydro-4H-furo[3,4-d][1,3]thiazin-2-amine which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
tert-Butyl ((4aS,5S,7aS)-7a-(5-bromo-2,4-difluorophenyl)-5-(fluoromethyl)-4a,5,7,7a-tetrahydro-4H-furo[3,4-d][1,3]thiazin-2-yl)carbamate; pyrimidine 5-boronic acid;
With
caesium carbonate;
bis-triphenylphosphine-palladium(II) chloride;
In
1,2-dimethoxyethane; ethanol; water;
at 100 ℃;
for 0.75h;
With
trifluoroacetic acid;
In
dichloromethane;
at 20 ℃;
for 1h;
With
ammonia;
In
methanol;
- Guidance literature:
-
Multi-step reaction with 11 steps
1.1: 2,2,6,6-tetramethyl-piperidine; n-butyllithium / hexane; tetrahydrofuran / 0.75 h / -75 °C / Inert atmosphere
1.2: 1 h / -78 °C
2.1: zinc; acetic acid / 20 °C
3.1: ammonium formate / palladium 10% on activated carbon / methanol / 20 °C / Inert atmosphere
4.1: dichloromethane / 1 h / 20 °C / Inert atmosphere
5.1: trifluoromethylsulfonic anhydride / pyridine / 2.17 h / -20 - 20 °C / Inert atmosphere
6.1: formic acid / water / 2.67 h / 20 °C
6.2: 0.5 h / 20 °C
7.1: Nonafluorobutanesulfonyl fluoride; triethylamine; triethylamine tris(hydrogen fluoride) / tetrahydrofuran / 2.17 h / 0 - 20 °C / Inert atmosphere; Cooling with ice
8.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / methanol / 20 - 65 °C / Inert atmosphere
9.1: N-Bromosuccinimide; sulfuric acid / sulfolane; trifluoroacetic acid / 0.75 h / 60 °C
10.1: triethylamine / tetrahydrofuran / 1 h / 100 °C
11.1: caesium carbonate / bis-triphenylphosphine-palladium(II) chloride / 1,2-dimethoxyethane; ethanol; water / 0.75 h / 100 °C
11.2: 1 h / 20 °C
With
2,2,6,6-tetramethyl-piperidine; N-Bromosuccinimide; n-butyllithium; formic acid; Nonafluorobutanesulfonyl fluoride; trifluoromethylsulfonic anhydride; sulfuric acid; ammonium formate; caesium carbonate; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine tris(hydrogen fluoride); triethylamine; zinc;
bis-triphenylphosphine-palladium(II) chloride; palladium 10% on activated carbon;
In
tetrahydrofuran; pyridine; sulfolane; methanol; 1,2-dimethoxyethane; ethanol; hexane; dichloromethane; water; trifluoroacetic acid;
- Guidance literature:
-
Multi-step reaction with 11 steps
1.1: 2,2,6,6-tetramethyl-piperidine; n-butyllithium / hexane; tetrahydrofuran / 0.75 h / -75 °C / Inert atmosphere
1.2: 1 h / -78 °C
2.1: zinc; acetic acid / 20 °C
3.1: ammonium formate / palladium 10% on activated carbon / methanol / 20 °C / Inert atmosphere
4.1: dichloromethane / 1 h / 20 °C / Inert atmosphere
5.1: trifluoromethylsulfonic anhydride / pyridine / 2.17 h / -20 - 20 °C / Inert atmosphere
6.1: formic acid / water / 2.67 h / 20 °C
6.2: 0.5 h / 20 °C
7.1: Nonafluorobutanesulfonyl fluoride; triethylamine; triethylamine tris(hydrogen fluoride) / tetrahydrofuran / 2.17 h / 0 - 20 °C / Inert atmosphere; Cooling with ice
8.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / methanol / 20 - 65 °C / Inert atmosphere
9.1: N-Bromosuccinimide; sulfuric acid / sulfolane; trifluoroacetic acid / 0.75 h / 60 °C
10.1: triethylamine / tetrahydrofuran / 1 h / 100 °C
11.1: caesium carbonate / bis-triphenylphosphine-palladium(II) chloride / 1,2-dimethoxyethane; ethanol; water / 0.75 h / 100 °C
11.2: 1 h / 20 °C
With
2,2,6,6-tetramethyl-piperidine; N-Bromosuccinimide; n-butyllithium; formic acid; Nonafluorobutanesulfonyl fluoride; trifluoromethylsulfonic anhydride; sulfuric acid; ammonium formate; caesium carbonate; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine tris(hydrogen fluoride); triethylamine; zinc;
bis-triphenylphosphine-palladium(II) chloride; palladium 10% on activated carbon;
In
tetrahydrofuran; pyridine; sulfolane; methanol; 1,2-dimethoxyethane; ethanol; hexane; dichloromethane; water; trifluoroacetic acid;
![tert-Butyl ((4aS,5S,7aS)-7a-(5-bromo-2,4-difluorophenyl)-5-(fluoromethyl)-4a,5,7,7a-tetrahydro-4H-furo[3,4-d][1,3]thiazin-2-yl)carbamate](/Databaselist/images/loading.webp)
