Sodium borohydride → 5-(3-fluorophenyl)-10-hydroxy-1,3-dimethyl-7,8,9,10-tetrahydropyrimido[4,5-a]indolizine-2,4(1H,3H)-dione

HRID 2201302Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2201302
[F:1][C:2]1[CH:3]=[C:4]([C:8]2[N:16]3[C:11]([C:12](=[O:17])[CH2:13][CH2:14][CH2:15]3)=[C:10]3[N:18]([CH3:25])[C:19](=[O:24])[N:20]([CH3:23])[C:21](=[O:22])[C:9]=23)[CH:5]=[CH:6][CH:7]=1.[BH4-].[Na+]>CO>[F:1][C:2]1[CH:3]=[C:4]([C:8]2[N:16]3[C:11]([CH:12]([OH:17])[CH2:13][CH2:14][CH2:15]3)=[C:10]3[N:18]([CH3:25])[C:19](=[O:24])[N:20]([CH3:23])[C:21](=[O:22])[C:9]=23)[CH:5]=[CH:6][CH:7]=1

Komponenten

4

Edukt 2

HCID 4311764Sodium borohydrideHCID 867235335-(3-Fluorophenyl)-1,3-dimethyl-8,9-dihydropyrimido[4,5-a]indolizine-2,4,10(1H,3H,7H)-trione

Produkt 1

HCID 867234235-(3-fluorophenyl)-10-hydroxy-1,3-dimethyl-7,8,9,10-tetrahydropyrimido[4,5-a]indolizine-2,4(1H,3H)-dione

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a stirred solution of 5-(3-fluorophenyl)-1,3-dimethyl-8,9-dihydropyrimido[4,5-a]indolizine-2,4,10(1H,3H,7H)-trione (step 1)(150 mg, 0.439 mmol) in MeOH (2197 μL) at 0° C. was added sodium borohydride (49.9 mg, 1.318 mmol) portionwise. The resulting yellow solution was warmed to room temperature and stirred for 15 minutes. The reaction was concentrated in vacuo. The residue was diluted with water (5 mL) and DCM (10 mL). The aqueous phase was separated and extracted with DCM (3×10 mL). The combined organic fractions were dried (Na2SO4) and concentrated under reduced pressure to afford the title compound as a pale yellow solid;

Aufarbeitung

  1. concentrationThe reaction was concentrated in vacuo
  2. additionThe residue was diluted with water (5 mL) and DCM (10 mL)
  3. customThe aqueous phase was separated
  4. extractionextracted with DCM (3×10 mL)
  5. dry with materialThe combined organic fractions were dried (Na2SO4)
  6. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-7d35bd3232cd4c6eb04dd308ee17be40
Quelldatensatz
uspto-grants-2016_06
Patentnummer
US09359381B2

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