반응 #1151497

반응 방정식

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

수율 79.0%

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

수율 79.0%

용매

MeOH

반응 조건

후처리

1. 1
   온도then heated at 90° C. for 90 minutes
2. 2
   기타The 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
   기타the volatiles were evaporated
6. 6
   workup.ADDITIONWater (20 ml) was added
7. 7
   여과the precipitated solid was collected by filtration
8. 8
   세척washed with water (2×10 ml)
9. 9
   workup.DISSOLUTIONThe residue was dissolved in MeOH (5 ml)
10. 10
    세척eluted with MeOH (30 ml)
11. 11
    workup.ADDITIONthe fractions containing product
12. 12
    기타were evaporated

실험 절차

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.

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