반응 #633812

반응 방정식

sodium hydroxide

water

diborane dimethyl sulphide

2-(4-{4,4-dimethyl-2,5-dioxo-3-[2-(pyridin-3-ylamino)pyridin-4-ylmethyl]imidazolidin-1-yl}-phenyl)-2-methylpropionic acid

→

3-[4-(2-hydroxy-1,1-dimethylethyl)phenyl]-5,5-dimethyl-1-{[2-(pyridin-3-ylamino)-pyridin-4-yl]methyl}imidazolidine-2,4-dione

수율 45.0%

용매

methanol

hydrochloric acid

ethyl acetate

tetrahydrofuran

반응 조건

후처리

1. 1
   농축concentrated under reduced pressure
2. 2
   기타The residue obtained
3. 3
   농축The solution is concentrated under reduced pressure
4. 4
   기타The residue obtained
5. 5
   기타is purified by Preparative LC/MS (gradient: acetonitrile/water/TFA 0.07%)
6. 6
   기타The product obtained
7. 7
   건조The organic phase is dried over magnesium sulphate
8. 8
   여과filtered
9. 9
   농축concentrated under reduced pressure

실험 절차

To a solution of 0.29 mL of diborane-dimethyl sulphide (2M in tetrahydrofuran) in 5 mL of tetrahydrofuran, under argon, at room temperature, is added 0.11 g of 2-(4-{4,4-dimethyl-2,5-dioxo-3-[2-(pyridin-3-ylamino)pyridin-4-ylmethyl]imidazolidin-1-yl}-phenyl)-2-methylpropionic acid obtained in stage f) below. The reaction medium is stirred at this same temperature for one hour and concentrated under reduced pressure. The residue obtained is taken up in 10 mL of methanol and 2 mL of 1N hydrochloric acid. The solution is concentrated under reduced pressure. The residue obtained is purified by Preparative LC/MS (gradient: acetonitrile/water/TFA 0.07%). The product obtained is taken up in 10 mL of ethyl acetate, 2 mL of water and 1 mL of 1N sodium hydroxide. The organic phase is dried over magnesium sulphate, filtered and then concentrated under reduced pressure to give 0.048 g of 3-[4-(2-hydroxy-1,1-dimethylethyl)phenyl]-5,5-dimethyl-1-{[2-(pyridin-3-ylamino)-pyridin-4-yl]methyl}imidazolidine-2,4-dione, the characteristics of which are as follows:

출처