Reaction #1810846

Reaction equation

2-Amino-4-(1-cyclopropylmethyl-2-methylimidazol-5-yl)pyrimidine

N-(2-methoxyethyl)-N-(t-butyl)-4-iodobenzenesulphonamide

acetic acid

→

title compound

Yield 32.2%

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

Yield 32.2%

Solvents

water

Conditions

Workup

1. 1
   Extractionextracted with EtOAc
2. 2
   Washwashed with water
3. 3
   Dryingbrine, dried
4. 4
   Otherthe solvent removed by evaporation
5. 5
   OtherThe residue was purified by chromatography on silica gel eluting with DCM/MeOH (97:3)

Procedure

2-Amino-4-(1-cyclopropylmethyl-2-methylimidazol-5-yl)pyrimidine (Method 54; 2 g, 8.73 mmol) was treated with N-(2-methoxyethyl)-N-(t-butyl)-4-iodobenzenesulphonamide (Method 77; 3.82 g, 9.61 mmol) under the conditions described in Example 22. The reaction was quenched by the addition of acetic acid (250 μl, 4.37 mmol), the mixture was poured into water and extracted with EtOAc. The extracts were combined, washed with water and then brine, dried and the solvent removed by evaporation. The residue was purified by chromatography on silica gel eluting with DCM/MeOH (97:3) to give the title compound (1.4 g, 32%) as a pale yellow foam. NMR: 0.01 (m, 2H) 0.18 (m, 2H) 1.90 (m, H) 2.26 (s, 3H) 3.15 (s, 3H) 3.37 (m, 4H) 4.42 (d, 2H) 7.08 (d, H) 7.52 (s, H) 7.58 (d, 2H) 7.75 (d, 2H) 8.30 (d, H) 9.75 (s, H); m/z 499.

Source