Reaction #355766

Reaction equation

2-methoxyethylamine

Chlorosulphonic acid

2-anilino-4-(1,2-diethylmethylimidazol-5-yl)pyrimidine

→

title compound

Yield 40.0%

4-(1,2-Diethyl-4-methylimidazol-5-yl)-2-{4-[N-(2-methoxyethyl)sulphamoyl]anilino}pyrimidine

Yield 40.0%

Solvents

isopropanol

thionyl chloride

Conditions

Workup

1. 1
   Temperaturethen heated at 90° C. for 90 minutes
2. 2
   OtherThe volatiles were removed by evaporation
3. 3
   Otherthe residue was dried under high vacuum (<2 mmHg) for 1 hour
4. 4
   workup.STIRRINGThe mixture was stirred for 30 minutes
5. 5
   Otherthe volatiles were evaporated in vacuo
6. 6
   workup.ADDITIONWater (20 ml) was added
7. 7
   Extractionextracted EtOAc (2×20ml)
8. 8
   Otherdried
9. 9
   Otherevaporated in vacuo

Procedure

Chlorosulphonic acid (150 μl, 2.16 mmol) was added dropwise to solution of 2-anilino-4-(1,2-diethylmethylimidazol-5-yl)pyrimidine (Method 13; 28 mg, 0.09 mmol) in thionyl chloride (2 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 2-methoxyethylamine (300 μl, 3.45 mmol) in isopropanol (2 ml) added. The mixture was stirred for 30 minutes and the volatiles were evaporated in vacuo. Water (20 ml) was added and extracted EtOAc (2×20ml). The organic layers were combined, dried and evaporated in vacuo to give the title compound (16 mg, 40%) as a orange solid. NMR 2.35-2.45 (m, 9H), 2.7 (q, 2H), 2.89 (q, 2H), 3.40-3.28 (m, 2H), 3.60-3.58 (m, 3H), 4.35 (m, 2H), 7.0 (d, 1H), 7.49 (t, 1H), 7.70 (d, 2H), 7.9 (d, 2H), 8.55 (d, 1H); m/z 445.

Source