Reaktion #1151497

Reaktionsgleichung

Chlorosulphonic acid

2-anilino-4-(1-ethyl-2-methylimidazol-5-yl)pyrimidine

2-Anilino-4-(1-ethyl-2-methylimidazol-5-yl)pyrimidine

thionyl chloride

2-(2-aminoethyl)ethanol

diethylmethylamine

→

title compound

Ausbeute 79.0%

4-(1-Ethyl-2-methylimidazol-5-yl)-2-(4-{N-[2-(2-hydroxyethoxy)ethyl]sulphamoyl}anilino)pyrimidine

Ausbeute 79.0%

Lösungsmittel

MeOH

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturthen heated at 90° C. for 90 minutes
2. 2
   SonstigeThe volatiles were removed by evaporation
3. 3
   workup.WAITthe resultant solid placed under high vacuum (<2 mmHg) for 1 hr
4. 4
   workup.STIRRINGThe solution was stirred for 30 minutes
5. 5
   Sonstigethe volatiles were evaporated
6. 6
   workup.ADDITIONWater (20 ml) was added
7. 7
   Filtrationthe precipitated solid was collected by filtration
8. 8
   Waschenwashed with water (2×10 ml)
9. 9
   workup.DISSOLUTIONThe residue was dissolved in MeOH (5 ml)
10. 10
    Wascheneluted with MeOH (30 ml)
11. 11
    workup.ADDITIONthe fractions containing product
12. 12
    Sonstigewere evaporated

Vorschrift

Chlorosulphonic acid (150 μl, 2.16 mmol) was added dropwise to a solution of 2-anilino-4-(1-ethyl-2-methylimidazol-5-yl)pyrimidine (Example 28; 150 mg, 0.54 mmol) in thionyl chloride (3 ml) cooled to 0° C. and the mixture stirred for 10 minutes at 0° C. then heated at 90° C. for 90 minutes. The volatiles were removed by evaporation and the resultant solid placed under high vacuum (<2 mmHg) for 1 hr. The resulting solid was placed under nitrogen and a solution of 2-(2-aminoethyl)ethanol (114 mg, 1.00 mmol) and diethylmethylamine in MeOH (3 ml) was cautiously added. The solution was stirred for 30 minutes and the volatiles were evaporated. Water (20 ml) was added and the precipitated solid was collected by filtration and washed with water (2×10 ml). The residue was dissolved in MeOH (5 ml) and loaded on to an Isolute amine column, eluted with MeOH (30 ml) and the fractions containing product were evaporated to give the title compound (190 mg, 79%) as a beige solid. NMR 1.18 (t, 3H), 2.39 (s, 3H), 2.89 (t, 2H), 3.15 (m, 7H), 4.38 (q, 2H), 7.21 (d, 1H), 7.71 (m, 3H), 7.89 (d, 2H), 8.41 (d, 1H), 9.82 (s, 1H); m/z 447.

Quelle