반응 #85643

반응 방정식

(2R,3S)-2-amino-3-(tert-butoxy)butan-1-ol

2,4,5-trifluoropyrimidine

DIEA

→

(2R,3S)-3-(tert-butoxy)-2-((2,5-difluoropyrimidin-4-yl)amino)butan-1-ol

수율 73.2%

용매

acetonitrile

반응 조건

후처리

1. 1
   기타The resulting reaction mixture
2. 2
   기타The volatiles were then removed
3. 3
   기타Reaction mixture
4. 4
   기타was then partitioned between EtOAc and water
5. 5
   추출Aqueous layer extracted with EtOAc
6. 6
   세척washed with water, brine
7. 7
   건조dried (Na2SO4)
8. 8
   여과filtered

실험 절차

To a round bottom flask containing (2R,3S)-2-amino-3-(tert-butoxy)butan-1-ol (1.25 g, 7.75 mmol) and a stir bar was added acetonitrile (50 mL) followed by the addition of 2,4,5-trifluoropyrimidine (1.04 g, 7.75 mmol) and DIEA (4.1 mL, 23.3 mmol). The resulting reaction mixture allowed to stir 1 hr at room temperature. The volatiles were then removed. Reaction mixture was then partitioned between EtOAc and water. Aqueous layer extracted with EtOAc. Organic phases combined, washed with water, brine, dried (Na2SO4), filtered and concentrated to a viscous yellow oil of (2R,3S)-3-(tert-butoxy)-2-((2,5-difluoropyrimidin-4-yl)amino)butan-1-ol (1.56 g, 5.67 mmol, 73% yield). 1H NMR (400 MHz, CDCl3) δ 1.15 (s, 9H) 1.32 (d, J=6.26 Hz, 3H) 3.45 (br. s., 1H) 3.67 (d, J=11.35 Hz, 1H) 3.85-3.92 (m, 1H) 4.27 (d, J=11.74 Hz, 1H) 6.29 (d, J=5.48 Hz, 1H) 7.87 (d, J=2.35 Hz, 1H). LCMS m/z 276.4 (M+H)+, Rt 0.71 min.

출처