Reaction #1596987

Reaction equation

2-aminopyrimidine

bromobenzene

BuLi

→

47

Yield 10.0%

4-Phenyl-pyrimidin-2-ylamine

Yield 10.0%

Solvents

toluene

THF

Conditions

Workup

1. 1
   workup.WAITthe mixture left
2. 2
   TemperatureThe mixture was refluxed for 16 h
3. 3
   Temperatureto cool to room temperature
4. 4
   Othercarefully quenched with aqueous NaHCO3
5. 5
   FiltrationThe mixture was filtered
6. 6
   Concentrationthe filtrate concentrated under vacuum
7. 7
   workup.DISSOLUTIONThe residue was then dissolved in DCM
8. 8
   Washwashed with aqueous NaHCO3, brine
9. 9
   Dryingdried (MgSO4)
10. 10
    OtherThe solvent was removed

Procedure

To a solution of bromobenzene (4.43 mL, 42.06 mmol) in dry THF (100 mL) at −78° C. was added BuLi (394 mL, 63.08 mmol) and the mixture left to stir at −78° C. for 2 h. To this was added 2-aminopyrimidine (2.0 g, 21.03 mmol) in hot toluene (80 mL) over a 15 minutes period. The mixture was refluxed for 16 h and allowed to cool to room temperature and carefully quenched with aqueous NaHCO3. The mixture was filtered and the filtrate concentrated under vacuum. The residue was then dissolved in DCM and washed with aqueous NaHCO3, brine and dried (MgSO4). The solvent was removed to afford 350 mg of 47 (10%) as a pale yellow solid: 1H NMR (400 MHz, CDCl3) δ 8.32 (d, J=4.8 Hz, 1H), 7.97 (m, 2H), 7.45 (m, 3H), 7.02 (J=4.8 Hz, 1H). 5.27 (br s, 2H); MS (+)-ES [M+H]+ 172.2 m/z.

Source