Réaction #1596987

Équation de réaction

2-aminopyrimidine

bromobenzene

BuLi

→

47

Rendement 10.0%

4-Phenyl-pyrimidin-2-ylamine

Rendement 10.0%

Solvants

toluene

THF

Conditions de réaction

Traitement

1. 1
   workup.WAITthe mixture left
2. 2
   TempératureThe mixture was refluxed for 16 h
3. 3
   Températureto cool to room temperature
4. 4
   Autrecarefully 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
   Lavagewashed with aqueous NaHCO3, brine
9. 9
   Séchagedried (MgSO4)
10. 10
    AutreThe solvent was removed

Mode opératoire

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