Adenine → 2-[1-(6-amino-9H-purin-9-yl)ethyl]-3-bromo-6-methyl-4H-pyrido[1,2-a]pyrimidin-4-one

HRID 1429767Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1429767
[Br:1][C:2]1[C:7](=[O:8])[N:6]2[C:9]([CH3:13])=[CH:10][CH:11]=[CH:12][C:5]2=[N:4][C:3]=1[CH:14](Cl)[CH3:15].[N:17]1[C:25]([NH2:26])=[C:24]2[C:20]([N:21]=[CH:22][NH:23]2)=[N:19][CH:18]=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[NH2:26][C:25]1[N:17]=[CH:18][N:19]=[C:20]2[C:24]=1[N:23]=[CH:22][N:21]2[CH:14]([C:3]1[N:4]=[C:5]2[CH:12]=[CH:11][CH:10]=[C:9]([CH3:13])[N:6]2[C:7](=[O:8])[C:2]=1[Br:1])[CH3:15]

Komponenten

6

Edukt 4

HCID 190AdenineHCID 962WaterHCID 11430Potassium CarbonateHCID 668640303-bromo-2-(1-chloroethyl)-6-methyl-4H-pyrido[1,2-a]pyrimidin-4-one

Produkt 1

HCID 668647722-[1-(6-amino-9H-purin-9-yl)ethyl]-3-bromo-6-methyl-4H-pyrido[1,2-a]pyrimidin-4-oneAusbeute 10,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of 3-bromo-2-(1-chloroethyl)-6-methyl-4H-pyrido[1,2-a]pyrimidin-4-one (1.24 g, 4.11 mmol), adenine (Sigma, 1.08 g, 8.04 mmol), and potassium carbonate (1.11 g, 8.04 mmol) in N,N-dimethylformamide (20 mL) was stirred at room temperature overnight. The suspension was then poured into water and extracted with methylene chloride. The combined organic layers were washed with water, brine, and then the organic layers dried and evaporated to dryness. The residue was chromatographed on silica gel, eluting with 0 to 10% MeOH in methylene chloride, to provide the desired product (176 mg, 10.7%). LCMS calculated for C16H15BrN7O (M+H)+: m/z=400.1. Found: 400.1. 1H NMR (DMSO-d6, 300 MHz) δ 8.44 (1H, s), 8.07 (1H, s), 7.67 (1H, dd, J=8.7 and 7.2 Hz), 7.30 (1H, br d, J=8.7 Hz), 7.20 (2H, s), 6.99 (1H, br d, J=7.2 Hz), 6.15 (1H, q, J=7.2 Hz), 2.91 (3H, s), 1.84 (3H, d, J=7.2 Hz) ppm.

Aufarbeitung

  1. extractionextracted with methylene chloride
  2. washThe combined organic layers were washed with water, brine
  3. customthe organic layers dried
  4. customevaporated to dryness
  5. customThe residue was chromatographed on silica gel
  6. washeluting with 0 to 10% MeOH in methylene chloride

Quellen und Nachweise

ORD-Eintrag
ord-f8aa0c754eee4b11831f8c594116f368
Quelldatensatz
uspto-grants-2015_01
Patentnummer
US08940752B2

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