Reaction #1810839

Reaction equation

Anisole

trifluoroacetic acid

4-(1-cyclopropylmethyl-2-ethylimidazol-5-yl)-2-{4-[N-(2-methoxyethyl)-N-(t-butyl)sulphamoyl]anilino}pyrimidine

→

title compound

Yield 48.0%

4-(1-Cyclopropylmethyl-2-ethylimidazol-5-yl )-2-{4-[N-(2-methoxyethyl) sulphamoyl]anilino}pyrimidine

Yield 48.0%

Conditions

Workup

1. 1
   Otherthe volatiles were evaporated
2. 2
   workup.DISSOLUTIONthe residue dissolved in water
3. 3
   Extractionextracted with EtOAc
4. 4
   Extractionextracted with EtOAc
5. 5
   OtherThe extract was dried
6. 6
   Otherthe solvent removed by evaporation
7. 7
   OtherThe residue was purified by chromatography on silica gel eluting with EtOAc/MeOH (100:0 increasing in polarity to 98:2)

Procedure

Anisole (4.57 ml) followed by trifluoroacetic acid (22 ml) was added to 4-(1-cyclopropylmethyl-2-ethylimidazol-5-yl)-2-{4-[N-(2-methoxyethyl)-N-(t-butyl)sulphamoyl]anilino}pyrimidine (Method 76; 3.7 g, 7.22 mmol). The mixture was stirred at ambient temperature for two hours, the volatiles were evaporated and the residue dissolved in water and then extracted with EtOAc. The aqueous layer was neutralised with saturated aqueous sodium hydrogen carbonate solution and extracted with EtOAc. The extract was dried and the solvent removed by evaporation. The residue was purified by chromatography on silica gel eluting with EtOAc/MeOH (100:0 increasing in polarity to 98:2) to give the title compound (1.58 g, 48%) as a foam. NMR: 0.00-0.02 m, 2H), 0.18-0.20 m, 2H), 0.86-0.90 (m, 1H), 1.10 (t, 3H), 2.60 (q, 2H), 2.75 (q, 2Hy, 3.01 (s, 3H>, 3.18 (q, 2H), 4.40 (d, 2H), 7.10 (d, 1H), 7.35 (t, 1H), 7.52 (s, 1H), 7.57 (d, 2H), 7.77 (d, 2H), 8.30 (d, 1H), 9.70 (s, 1H); m/z 457.

Source