反応 #66601

反応方程式

triethylsilane

(2,4-diamino-pyrimidin-5-yl)-[4,5-dimethoxy-2-(1-methyl-2-phenyl-ethyl)-phenyl]methanone

LiAlH4

trifluoroacetic acid

K2CO3

→

5-[4,5-dimethoxy-2-(1-methyl-2-phenyl-ethyl)-benzyl]-pyrimidine-2,4-diamine

収率 58.0%

溶媒

THF

CH2Cl2

反応条件

後処理

1. 1
   温度was warmed to reflux
2. 2
   その他quenched by the Fieser method
3. 3
   ろ過After 30 min the mixture was filtered through a pad of celite
4. 4
   濃縮concentrated in vacuo
5. 5
   その他to give a crude white solid
6. 6
   workup.ADDITIONas added
7. 7
   抽出the mixture was extracted with ethyl acetate
8. 8
   洗浄washed with brine
9. 9
   乾燥The combined organics were dried over Na2SO4
10. 10
    ろ過filtered
11. 11
    濃縮concentrated in vacuo
12. 12
    その他Purification via flash chromatography (95:5 CH2Cl2)

実験手順

To a solution of (2,4-diamino-pyrimidin-5-yl)-[4,5-dimethoxy-2-(1-methyl-2-phenyl-ethyl)-phenyl]methanone (0.413 g, 0.4 mmol) in 10 mL THF was added LiAlH4 (0.73 mL, 1.0 M in THF) over 5 min. After gas evolution ceased the mixture was warmed to reflux. After 3 h the mixture was cooled to 0° C. and quenched by the Fieser method. After 30 min the mixture was filtered through a pad of celite and concentrated in vacuo to give a crude white solid. To a solution of this solid in 5 mL CH2Cl2 was added trifluoroacetic acid (1.1 mL, 14.0 mmol) followed by triethylsilane (0.4 mL, 2.8 mmol). After 30 min 50 mL 10% K2CO3 was as added and the mixture was extracted with ethyl acetate and washed with brine. The combined organics were dried over Na2SO4, filtered and concentrated in vacuo. Purification via flash chromatography (95:5 CH2Cl2) afforded 5-[4,5-dimethoxy-2-(1-methyl-2-phenyl-ethyl)-benzyl]-pyrimidine-2,4-diamine (0.066 g, 58%) as a white foam; melting point (HCl salt) 227.1-227-4° C.

出典