Dimethylformamide → 2-(1,3-dimethyl-2,6-dioxo-1,2,3,6-tetrahydropurin-7-yl)-N-(4-isopropylphenyl)-N-methylacetamide

HRID 44425

Reaktionsgleichung

Reaktionsgleichung von HRID 44425
[N:1]1([C:12](=[O:13])[C:11]2[N:10]([CH2:14][C:15]([OH:17])=O)[CH:9]=[N:8][C:7]=2[N:5]([CH3:6])[C:3]1=[O:4])[CH3:2].C(Cl)(=O)C(Cl)=O.CN(C=O)C.[CH3:29][NH:30][C:31]1[CH:36]=[CH:35][C:34]([CH:37]([CH3:39])[CH3:38])=[CH:33][CH:32]=1>C(Cl)(Cl)Cl.CC#N>[CH3:2][N:1]1[C:12](=[O:13])[C:11]2[N:10]([CH2:14][C:15]([N:30]([C:31]3[CH:36]=[CH:35][C:34]([CH:37]([CH3:39])[CH3:38])=[CH:33][CH:32]=3)[CH3:29])=[O:17])[CH:9]=[N:8][C:7]=2[N:5]([CH3:6])[C:3]1=[O:4]

Komponenten

7

Edukt 4

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 69550AcefyllineHCID 138880Aniline, p-isopropyl-N-methyl-

Produkt 1

HCID 592051082-(1,3-dimethyl-2,6-dioxo-1,2,3,6-tetrahydropurin-7-yl)-N-(4-isopropylphenyl)-N-methylacetamideAusbeute 84,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6212ChloroformLösungsmittel2×HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

To a solution of acid 101 (0.5 g, 2.1 mmol) in CHCl3 (30 mL) and CH3CN (30 mL) at 0° C. was added oxalyl chloride (1.59 g, 12.6 mmol) and a catalytic amount of DMF. The resulting solution was stirred for 2 h at rt and concentrated in vacuo. The resulting residue was re-dissolved in CHCl3 and cooled to 0° C. To this mixture was added N-methyl-4-isopropyl aniline (0.78 g, 5.2 mmol) and the reaction was stirred overnight warming to rt. The reaction mixture was diluted with CHCl3 (30 mL) and washed with 1 N HCl (50 mL). The combined organic layers were washed with water (75 mL), dried over Na2SO4 and concentrated in vacuo. The product was purified by chromatography on silica gel eluting with EtOAc/hexanes and EtOAc/MeOH to yield 393 as a light yellow solid (0.65 g, 84.4%). mp: 231-233° C. MS (APCI): m/z 370.2 [M+H]+. Anal. Calcd. For C19H23N5O3. 0.1 H2O: C, 61.47; H, 6.30; N, 18.87. Found C, 61.28; H, 6.19; N, 18.57.

Aufarbeitung

  1. concentrationconcentrated in vacuo
  2. dissolutionThe resulting residue was re-dissolved in CHCl3
  3. temperaturecooled to 0° C
  4. stirringthe reaction was stirred overnight
  5. temperaturewarming to rt
  6. washwashed with 1 N HCl (50 mL)
  7. washThe combined organic layers were washed with water (75 mL)
  8. dry with materialdried over Na2SO4
  9. concentrationconcentrated in vacuo
  10. customThe product was purified by chromatography on silica gel eluting with EtOAc/hexanes and EtOAc/MeOH

Quellen und Nachweise

ORD-Eintrag
ord-520aa4812d404776bd4a5f1a0249eccd
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08541423B2

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