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Methyl iodide → 3-butyl-1-methyl-7-(2-propen-1-yl)-3,7-dihydro-1H-purine-2,6-dione

HRID 1943800
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1943800
[CH2:1]([N:5]1[C:13]2[N:12]=[CH:11][N:10]([CH2:14][CH:15]=[CH2:16])[C:9]=2[C:8](=[O:17])[NH:7][C:6]1=[O:18])[CH2:2][CH2:3][CH3:4].[C:19]([O-])([O-])=O.[Na+].[Na+].CI.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH2:1]([N:5]1[C:13]2[N:12]=[CH:11][N:10]([CH2:14][CH:15]=[CH2:16])[C:9]=2[C:8](=[O:17])[N:7]([CH3:19])[C:6]1=[O:18])[CH2:2][CH2:3][CH3:4]
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Komponenten

6

Edukt 4

HCID 6328Methyl iodide2×HCID 10340Sodium CarbonateHCID 11430Potassium CarbonateHCID 592995893-butyl-7-(2-propen-1-yl)-3,7-dihydro-1H-purine-2,6-dione

Produkt 1

HCID 592995393-butyl-1-methyl-7-(2-propen-1-yl)-3,7-dihydro-1H-purine-2,6-dioneAusbeute 117,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
35 °C

Versuchsvorschrift

A stirred solution of 3-butyl-7-(2-propen-1-yl)-3,7-dihydro-1H-purine-2,6-dione (1.0 g, 4.03 mmol) in anhydrous DMF (10 ml) was treated with Na2CO3 (470 mg, 4.43 mmol) followed by Methyliodide (275 ul, 4.43 mmol). The mixture was heated at 35° C. for 17 hours. K2CO3 (500 mg, 3.6 mmol) and Methyliodide (275 ul, 4.43 mmol) were added and then stirred at 50° C. for a further 18 hours. The reaction mixture was allowed to cool then partitioned between 2M HCl (aq) and EtOAc. The organic layer was separated and the aqueous extracted once more with EtOAc. The combined extracts were washed with brine, dried (MgSO4) and concentrated giving a yellow/brown oil (1.24 g). The product was purified by silica SPE (10 g), eluting with EtOAc/cyclohexane mixtures. The product fractions were combined and concentrated to afford the title compound as a pale yellow solid (1.11 g, quant.); m/z 263.3[MH+].

Aufarbeitung

  1. temperatureto cool
  2. customthen partitioned between 2M HCl (aq) and EtOAc
  3. customThe organic layer was separated
  4. extractionthe aqueous extracted once more with EtOAc
  5. washThe combined extracts were washed with brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-953699045fbd45e085cf7a914855e2e1
Quelldatensatz
uspto-grants-2013_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08394808B2

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