Reaction #1810843

Reaction equation

water

5-(3-Dimethylaminoprop-2-en-1-oyl)-1-cyclobutyl-2-methylimidazole

5-(3-Dimethylaminoprop-2-enoyl)-1-cyclobutyl-2-methylimidazole

phenylguanidine hydrogen carbonate

sodium methoxide

→

title compound

Yield 35.0%

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

Yield 35.0%

Solvents

DMA

Conditions

Workup

1. 1
   Temperatureto cool to ambient temperature
2. 2
   ExtractionThe solution was extracted EtOAc (2×50 ml)
3. 3
   WashThe combined extracts were washed with water (2×50 ml)
4. 4
   Dryingbrine (2×50 ml), dried
5. 5
   Otherthe volatiles removed by evaporation
6. 6
   OtherThe residue was triturated with ether
7. 7
   Filtrationcollected by filtration and air
8. 8
   Otherdried

Procedure

5-(3-Dimethylaminoprop-2-en-1-oyl)-1-cyclobutyl-2-methylimidazole (Method 37; 466 mg, 2 mmol), phenylguanidine hydrogen carbonate (434 g, 2.2 mmol) and sodium methoxide (238 mg, 4.4 mmol) were suspended in anhydrous DMA (5 ml) and the mixture heated at 160° C. for 3 hours. The reaction mixture was allowed to cool to ambient temperature and poured into water (50 ml). The solution was extracted EtOAc (2×50 ml). The combined extracts were washed with water (2×50 ml) and then brine (2×50 ml), dried and the volatiles removed by evaporation. The residue was triturated with ether, collected by filtration and air dried to give the title compound (205 mg, 35%) as a brown solid. NMR: 1.63 (m, 2H), 2.35 (m, 4H), 2.53 (s, 3H), 5.5 (m, 1H), 6.96 (d, 2H), 7.28 (m, 4H), 7.70 (d, 2H), 8.39 (d, 1H), 9/45 (s, 1H); m/z 306.

Source