반응 #1596987

반응 방정식

2-aminopyrimidine

bromobenzene

BuLi

→

47

수율 10.0%

4-Phenyl-pyrimidin-2-ylamine

수율 10.0%

용매

toluene

THF

반응 조건

후처리

1. 1
   workup.WAITthe mixture left
2. 2
   온도The mixture was refluxed for 16 h
3. 3
   온도to cool to room temperature
4. 4
   기타carefully quenched with aqueous NaHCO3
5. 5
   여과The mixture was filtered
6. 6
   농축the filtrate concentrated under vacuum
7. 7
   workup.DISSOLUTIONThe residue was then dissolved in DCM
8. 8
   세척washed with aqueous NaHCO3, brine
9. 9
   건조dried (MgSO4)
10. 10
    기타The solvent was removed

실험 절차

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.

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