تفاعل #1596987

معادلة التفاعل

2-aminopyrimidine

bromobenzene

BuLi

→

47

المردود 10.0%

4-Phenyl-pyrimidin-2-ylamine

المردود 10.0%

المذيبات

toluene

THF

ظروف التفاعل

المعالجة

1. 1
   workup.WAITthe mixture left
2. 2
   درجة الحرارةThe mixture was refluxed for 16 h
3. 3
   درجة الحرارةto cool to room temperature
4. 4
   أخرىcarefully quenched with aqueous NaHCO3
5. 5
   ترشيحThe mixture was filtered
6. 6
   تركيزthe filtrate concentrated under vacuum
7. 7
   workup.DISSOLUTIONThe residue was then dissolved in DCM
8. 8
   غسيلwashed with aqueous NaHCO3, brine
9. 9
   تجفيفdried (MgSO4)
10. 10
    أخرىThe solvent was removed

الإجراء التجريبي

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.

المصدر