반응 #155647

반응 방정식

CH2Cl2

sodium borohydride

2-(6-tert-butyl-1-oxo-1H-phthalazin-2-yl)-6-{1-methyl-5-[5-(morpholine-4-carbonyl)-pyridin-2-ylamino]-6-oxo-1,6-dihydro-pyridin-3-yl}-benzaldehyde

CH2Cl2

→

title compound

수율 76.5%

6-tert-Butyl-2-(2-hydroxymethyl-3-{1-methyl-5-[5-(morpholine-4-carbonyl)-pyridin-2-ylamino]-6-oxo-1,6-dihydro-pyridin-3-yl}-phenyl)-2H-phthalazin-1-one

수율 76.5%

용매

MeOH

MeOH

반응 조건

후처리

1. 1
   기타vial fitted with a stir bar
2. 2
   기타to obtain a clear amber solution
3. 3
   workup.STIRRINGStirred at room temperature for 3 hr
4. 4
   기타Quenched
5. 5
   기타the reaction with 5 mL of saturated aqueous NH4Cl
6. 6
   기타separated phases
7. 7
   세척Washed the organic phase with 5 mL brine
8. 8
   건조dried over Na2SO4
9. 9
   기타removed the solvent on rotavap
10. 10
    workup.ADDITIONAdded 2 mL acetonitrile to the residue
11. 11
    workup.DISSOLUTIONThe residue dissolved momentarily
12. 12
    기타a white precipitate rapidly crystallized out of solution
13. 13
    workup.ADDITIONAdded 5 mL Et2O to the mixture
14. 14
    기타collected the precipitate
15. 15
    여과by filtration
16. 16
    기타Dried under high vacuum

실험 절차

121 mg (0.20 mmol) of 2-(6-tert-butyl-1-oxo-1H-phthalazin-2-yl)-6-{1-methyl-5-[5-(morpholine-4-carbonyl)-pyridin-2-ylamino]-6-oxo-1,6-dihydro-pyridin-3-yl}-benzaldehyde was weighed into a 20 mL reaction vial fitted with a stir bar and septum. Added 4 mL of CH2Cl2 and 2 mL MeOH and stirred to obtain a clear amber solution. Added 1.1 mL (0.29 mmol) of a freshly prepared 10 mg/mL solution of sodium borohydride in MeOH. Stirred at room temperature for 3 hr. Quenched the reaction with 5 mL of saturated aqueous NH4Cl. Added 5 mL of CH2Cl2 to the reaction mixture and separated phases. Washed the organic phase with 5 mL brine, dried over Na2SO4, and removed the solvent on rotavap. Added 2 mL acetonitrile to the residue and immersed the vial in an ultrasonic bath. The residue dissolved momentarily, then a white precipitate rapidly crystallized out of solution. Added 5 mL Et2O to the mixture and collected the precipitate by filtration. Dried under high vacuum to obtain 95 mg of the title compound as an off-white solid. MS (ESI) 621 (M+H)+.

출처