Reaction #355770

Reaction equation

n-butyl lithium

hexane

Iodomethane

n-butyl lithium

hexane

2-Anilino4-(l-ethyl-2,4dimethylimidazol-5-yl)pyrimidine

2-Anilino-4-(1-ethyl-2,4dimethylimidazol-5-yl)pyrimidine

→

title compound

Yield 13.0%

2-Anilino-4(1,2-diethyl-4-methlimidazol-5-yl)pyrimidine

Yield 13.0%

Solvents

water

THF

Conditions

Workup

1. 1
   TemperatureThe stirring solution was cooled
2. 2
   Otherto −70° C
3. 3
   Othertemperature <−60° C.
4. 4
   Temperaturethe temperature was maintained at −70° C. for an additional 10 minutes
5. 5
   Otherto rise to room temperature
6. 6
   workup.ADDITIONwas added
7. 7
   ExtractionThe aqueous layer extracted with EtOAc (2×20 ml)
8. 8
   Otherdried solvent evaporated in vacuo
9. 9
   OtherThe residue was purified by flash silica chromatography DCM

Procedure

2-Anilino4-(l-ethyl-2,4dimethylimidazol-5-yl)pyrimidine (Method 11; 200 mg, 0.68 mmol) was dissolved in anhydrous THF (10 ml) under an inert atmosphere. The stirring solution was cooled using dry-ice/acetone bath to −70° C. A 1.6 M solution of n-butyl lithium in hexane (900 μl, 1.44 mmol) was added drop-wise keeping temperature <−60° C. until the dark red colour remained. At this point 1.6 M n-butyl lithium in hexane (450 μl, 0.72 mmol) was added and the solution stirred at −70° C. for 10 minutes. Iodomethane (99 μl, 1.50 mmol) was added, the temperature was maintained at −70° C. for an additional 10 minutes then allowed to rise to room temperature. The reaction was allowed to stir for 1 hr at room temperature when water (100 ml) was added. The aqueous layer extracted with EtOAc (2×20 ml). Organics were combined, dried solvent evaporated in vacuo. The residue was purified by flash silica chromatography DCM:MeOH (increasing in polarity from 100:0 to 96:4) to yield the title compound (28 mg, 13%). M/z 322.

Source