Technology Process of (4S)-4-{4-Cyano-2-[(1,3-thiazol-4-ylmethyl)sulfonyl]phenyl}-3,6-dimethyl-2-oxo-1-[3-(trifluoromethyl)phenyl]-1,2,3,4-tetrahydropyrimidine-5-carbonitrile
There total 10 articles about (4S)-4-{4-Cyano-2-[(1,3-thiazol-4-ylmethyl)sulfonyl]phenyl}-3,6-dimethyl-2-oxo-1-[3-(trifluoromethyl)phenyl]-1,2,3,4-tetrahydropyrimidine-5-carbonitrile 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:
- Guidance literature:
-
With
18-crown-6 ether; potassium carbonate; potassium iodide;
In
N,N-dimethyl-formamide;
at 100 - 110 ℃;
for 17h;
Molecular sieve;
Inert atmosphere;
sealed tube;
- Guidance literature:
-
Multi-step reaction with 10 steps
1.1: triethyl phosphate / tetrahydrofuran / 16 h / Inert atmosphere; Reflux
2.1: morpholine / tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran / 2 h / 20 °C / Inert atmosphere
3.1: chiral silica gel phase based on the selector poly(N-methacryloyl-L-leucine-tert-butylamide); column dimensions: 670 mm x 40 mm / ethyl acetate; methanol / 24 °C / Resolution of racemate
4.1: dmap; N-ethyl-N,N-diisopropylamine; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate / tetrahydrofuran / 20 °C / Inert atmosphere
4.2: 1 h / 20 °C
5.1: methoxycarbonylsulfamoyl-triethylammmonium hydroxide / tetrahydrofuran / 2 h / 20 °C / Inert atmosphere
6.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere
6.2: 16 h / -78 - 20 °C
7.1: hydrogen / palladium 10% on activated carbon / methanol / 5.5 h / 20 °C / 760.05 Torr / Inert atmosphere
8.1: hydrogenchloride; sodium nitrite; acetic acid / water / 0.67 h / -10 - -5 °C / Inert atmosphere
8.2: 1.5 h / -10 - 15 °C
9.1: sodium hydrogencarbonate; sodium sulfite / tetrahydrofuran / 1 h / 20 °C
10.1: potassium carbonate; potassium iodide; 18-crown-6 ether / N,N-dimethyl-formamide / 17 h / 100 - 110 °C / Molecular sieve; Inert atmosphere; sealed tube
With
morpholine; hydrogenchloride; dmap; methoxycarbonylsulfamoyl-triethylammmonium hydroxide; 18-crown-6 ether; triethyl phosphate; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; hydrogen; sodium hydrogencarbonate; potassium carbonate; acetic acid; N-ethyl-N,N-diisopropylamine; potassium iodide; lithium hexamethyldisilazane; sodium sulfite; sodium nitrite;
tetrakis(triphenylphosphine) palladium(0); palladium 10% on activated carbon;
In
tetrahydrofuran; methanol; water; ethyl acetate; N,N-dimethyl-formamide;
- Guidance literature:
-
Multi-step reaction with 10 steps
1.1: triethyl phosphate / tetrahydrofuran / 16 h / Inert atmosphere; Reflux
2.1: morpholine / tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran / 2 h / 20 °C / Inert atmosphere
3.1: chiral silica gel phase based on the selector poly(N-methacryloyl-L-leucine-tert-butylamide); column dimensions: 670 mm x 40 mm / ethyl acetate; methanol / 24 °C / Resolution of racemate
4.1: dmap; N-ethyl-N,N-diisopropylamine; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate / tetrahydrofuran / 20 °C / Inert atmosphere
4.2: 1 h / 20 °C
5.1: methoxycarbonylsulfamoyl-triethylammmonium hydroxide / tetrahydrofuran / 2 h / 20 °C / Inert atmosphere
6.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere
6.2: 16 h / -78 - 20 °C
7.1: hydrogen / palladium 10% on activated carbon / methanol / 5.5 h / 20 °C / 760.05 Torr / Inert atmosphere
8.1: hydrogenchloride; sodium nitrite; acetic acid / water / 0.67 h / -10 - -5 °C / Inert atmosphere
8.2: 1.5 h / -10 - 15 °C
9.1: sodium hydrogencarbonate; sodium sulfite / tetrahydrofuran / 1 h / 20 °C
10.1: potassium carbonate; potassium iodide; 18-crown-6 ether / N,N-dimethyl-formamide / 17 h / 100 - 110 °C / Molecular sieve; Inert atmosphere; sealed tube
With
morpholine; hydrogenchloride; dmap; methoxycarbonylsulfamoyl-triethylammmonium hydroxide; 18-crown-6 ether; triethyl phosphate; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; hydrogen; sodium hydrogencarbonate; potassium carbonate; acetic acid; N-ethyl-N,N-diisopropylamine; potassium iodide; lithium hexamethyldisilazane; sodium sulfite; sodium nitrite;
tetrakis(triphenylphosphine) palladium(0); palladium 10% on activated carbon;
In
tetrahydrofuran; methanol; water; ethyl acetate; N,N-dimethyl-formamide;
![sodium 5-cyano-2-{(4S)-5-cyano-3,6-dimethyl-2-oxo-1-[3-(trifluoromethyl)phenyl]-1,2,3,4-tetrahydropyrimidin-4-yl}benzenesulfinate](/Databaselist/images/loading.webp)
