反応 #1596987

反応方程式

2-aminopyrimidine

bromobenzene

BuLi

→

47

収率 10.0%

4-Phenyl-pyrimidin-2-ylamine

収率 10.0%

溶媒

toluene

THF

反応条件

後処理

1. 1
   workup.WAITthe mixture left
2. 2
   温度The mixture was refluxed for 16 h
3. 3
   温度to cool to room temperature
4. 4
   その他carefully quenched with aqueous NaHCO3
5. 5
   ろ過The mixture was filtered
6. 6
   濃縮the filtrate concentrated under vacuum
7. 7
   workup.DISSOLUTIONThe residue was then dissolved in DCM
8. 8
   洗浄washed with aqueous NaHCO3, brine
9. 9
   乾燥dried (MgSO4)
10. 10
    その他The solvent was removed

実験手順

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.

出典