Reaktion #2204925

Reaktionsgleichung

Chlorosulphonic acid

2-anilino-4-(1-methyl-2-isopropylimidazol-5-yl)pyrimidine

cyclobutylamine

diethylmethylamine

→

title compound

Ausbeute 65.6%

4-(1-Methyl-2-isopropylimidazol-5-yl)-2-{4-[N-(cyclobutyl)sulphamoyl]anilino}pyrimidine

Ausbeute 65.6%

Lösungsmittel

thionyl chloride

MeOH

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturthen heated at 90° C. for 90 minutes
2. 2
   SonstigeThe volatiles were removed by evaporation
3. 3
   Sonstigethe residue was dried under high vacuum (<2 mmHg) for 1 hour
4. 4
   workup.STIRRINGThe mixture was stirred for 30 minutes
5. 5
   Sonstigethe volatiles were evaporated in vacuo
6. 6
   SonstigeTrituration with water results in a solid which
7. 7
   Waschenwas washed water (3×20 ml)
8. 8
   Filtrationcollected by filtration
9. 9
   Sonstigedried under vacuum at 60° C.

Vorschrift

Chlorosulphonic acid (150 μl, 2.16 mmol) was added dropwise to solution of 2-anilino-4-(1-methyl-2-isopropylimidazol-5-yl)pyrimidine (Method 71; 158 mg, 0.54 mmol) in thionyl chloride (3 ml) cooled at 0° C. and the mixture stirred at 0° C. for 10 minutes then heated at 90° C. for 90 minutes. The volatiles were removed by evaporation and the residue was dried under high vacuum (<2 mmHg) for 1 hour. The resulting solid was placed under nitrogen and a solution of cyclobutylamine (100 μl, 1.08 mmol) and diethylmethylamine (1 ml, 15 mmol) in MeOH (3 ml) added. The mixture was stirred for 30 minutes and the volatiles were evaporated in vacuo. Trituration with water results in a solid which was washed water (3×20 ml) collected by filtration and dried under vacuum at 60° C. to yield the title compound (151 mg, 65%) as a solid. NMR: 1.24 (d, 6H), 1.45 (m, 2H), 1.70 (m, 2H), 1.90 (m, 2H), 3.17 (m, 1H), 3.58 (m, 1H), 3.98 (s, 3H), 7.19 (d, 1H), 7.70 (m, 4H), 7.92 (d, 2H), 8.41 (d, 1H), 9.90 (brs, 1H); m/z 427.

Quelle