反応 #85643

反応方程式

(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

収率 73.2%

溶媒

acetonitrile

反応条件

後処理

1. 1
   その他The resulting reaction mixture
2. 2
   その他The volatiles were then removed
3. 3
   その他Reaction mixture
4. 4
   その他was then partitioned between EtOAc and water
5. 5
   抽出Aqueous layer extracted with EtOAc
6. 6
   洗浄washed with water, brine
7. 7
   乾燥dried (Na2SO4)
8. 8
   ろ過filtered

実験手順

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.

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