Ethyl Acetate → 2-(1-aminopropyl)-3-iodo-6-methyl-4H-pyrido[1,2-a]pyrimidin-4-one

HRID 58229

Reaktionsgleichung

Reaktionsgleichung von HRID 58229
[N:1]([CH:4]([C:7]1[N:8]=[C:9]2[CH:18]=[CH:17][CH:16]=[C:15]([CH3:19])[N:10]2[C:11](=[O:14])[C:12]=1[I:13])[CH2:5][CH3:6])=[N+]=[N-].CP(C)C.CCOC(C)=O>O1CCCC1.O>[NH2:1][CH:4]([C:7]1[N:8]=[C:9]2[CH:18]=[CH:17][CH:16]=[C:15]([CH3:19])[N:10]2[C:11](=[O:14])[C:12]=1[I:13])[CH2:5][CH3:6]

Komponenten

6

Edukt 3

HCID 8857Ethyl AcetateHCID 68983TrimethylphosphineHCID 866500622-(1-azidopropyl)-3-iodo-6-methyl-4H-pyrido[1,2-a]pyrimidin-4-one

Produkt 1

HCID 668638382-(1-aminopropyl)-3-iodo-6-methyl-4H-pyrido[1,2-a]pyrimidin-4-one

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a stirred solution of 2-(1-azidopropyl)-3-iodo-6-methyl-4H-pyrido[1,2-a]pyrimidin-4-one (3.10 g, 8.40 mmol) in tetrahydrofuran (20 mL) and water (6.06 mL) was added a 1.0 M solution of trimethylphosphine in tetrahydrofuran (0.1 mmol) at room temperature and stirred for 1 hour. To the mixture was added EtOAc and the mixture was extracted twice with 1 N HCl. The combined extracts were neutralized with solid sodium bicarbonate and extracted with methylene chloride. The combined organic layers were washed with brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was used directly in next step (2.58 g, 89.5%). LCMS calculated for C12H15IN3O (M+H)+: m/z=344.0. Found: 344.2.

Aufarbeitung

  1. extractionthe mixture was extracted twice with 1 N HCl
  2. extractionextracted with methylene chloride
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-9fe9c0f779b44f3eb27919e12ed66e9c
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09434746B2

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