Reaktion #155647

Reaktionsgleichung

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

Ausbeute 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

Ausbeute 76.5%

Lösungsmittel

MeOH

MeOH

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigevial fitted with a stir bar
2. 2
   Sonstigeto obtain a clear amber solution
3. 3
   workup.STIRRINGStirred at room temperature for 3 hr
4. 4
   SonstigeQuenched
5. 5
   Sonstigethe reaction with 5 mL of saturated aqueous NH4Cl
6. 6
   Sonstigeseparated phases
7. 7
   WaschenWashed the organic phase with 5 mL brine
8. 8
   Trocknendried over Na2SO4
9. 9
   Sonstigeremoved the solvent on rotavap
10. 10
    workup.ADDITIONAdded 2 mL acetonitrile to the residue
11. 11
    workup.DISSOLUTIONThe residue dissolved momentarily
12. 12
    Sonstigea white precipitate rapidly crystallized out of solution
13. 13
    workup.ADDITIONAdded 5 mL Et2O to the mixture
14. 14
    Sonstigecollected the precipitate
15. 15
    Filtrationby filtration
16. 16
    SonstigeDried under high vacuum

Vorschrift

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)+.

Quelle