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Dimethylamine → N'-(5-Mesityl-3,7-dimethyl-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidin-2-yl)-N,N-dimethylurea

HRID 598129
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 598129
[NH2:1][C:2]1[N:3]([CH3:22])[C:4](=[O:21])[C:5]2[C:10]([C:11]3[C:16]([CH3:17])=[CH:15][C:14]([CH3:18])=[CH:13][C:12]=3[CH3:19])=[CH:9][N:8]([CH3:20])[C:6]=2[N:7]=1.ClC(OC1C=CC([N+]([O-])=O)=CC=1)=[O:25].[CH2:36]([N:38]([CH2:41]C)[CH2:39]C)C.CNC>O1CCCC1>[C:12]1([CH3:19])[CH:13]=[C:14]([CH3:18])[CH:15]=[C:16]([CH3:17])[C:11]=1[C:10]1[C:5]2[C:4](=[O:21])[N:3]([CH3:22])[C:2]([NH:1][C:36](=[O:25])[N:38]([CH3:41])[CH3:39])=[N:7][C:6]=2[N:8]([CH3:20])[CH:9]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 674DimethylamineHCID 8471TriethylamineHCID 821294-Nitrophenyl chloroformateHCID 672673282-Amino-5-mesityl-3,7-dimethyl-3,7-dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-one

Produkt 1

HCID 58938580N'-(5-Mesityl-3,7-dimethyl-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidin-2-yl)-N,N-dimethylureaAusbeute 24,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a solution of 2-amino-5-mesityl-3,7-dimethyl-3,7-dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-one (0.040 g, 0.135 mmol) in tetrahydrofuran (1 mL) were added p-nitrophenyl chloroformate (0.073 g, 0.361 mmol) and triethylamine (0.050 mL, 0.361 mmol), and the mixture was allowed to stir at 60° C. for 2 hours. A 2M solution of dimethylamine in tetrahydrofuran (0.4 mL) was added to the mixture, followed by stirring at 60° C. for 15 hours. After cooling, the reaction mixture was diluted with ice-cold water and extracted with ethyl acetate. The organic layer was washed with water and brine, dried over sodium sulfate and concentrated in vacuo. The residue was purified by silica gel column chromatography eluting with hexane/ethyl acetate (4:1-1:2). The desired fractions were concentrated in vacuo, and the residual crystals were washed with diisopropyl ether-diethyl ether to give 0.012 g (24%) of the title compound.

Aufarbeitung

  1. stirringby stirring at 60° C. for 15 hours
  2. temperatureAfter cooling
  3. additionthe reaction mixture was diluted with ice-cold water
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with water and brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by silica gel column chromatography
  9. washeluting with hexane/ethyl acetate (4:1-1:2)
  10. concentrationThe desired fractions were concentrated in vacuo
  11. washthe residual crystals were washed with diisopropyl ether-diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-ceba88ea64824390a60aa5038658f08b
Quelldatensatz
uspto-grants-2011_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07897607B2

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