4-Aminopyrimidine → 8-Methoxy-2-oxo-2H-chromene-3-carboxylic acid pyrimidin-4-ylamide

HRID 240016

Reaktionsgleichung

Reaktionsgleichung von HRID 240016
CCN(C(C)C)C(C)C.[CH3:10][O:11][C:12]1[CH:13]=[CH:14][CH:15]=[C:16]2[C:21]=1[O:20][C:19](=[O:22])[C:18]([C:23]([OH:25])=O)=[CH:17]2.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[N:50]1[CH:55]=[CH:54][C:53]([NH2:56])=[N:52][CH:51]=1>CN(C)C=O>[N:50]1[CH:55]=[CH:54][C:53]([NH:56][C:23]([C:18]2[C:19](=[O:22])[O:20][C:21]3[C:16]([CH:17]=2)=[CH:15][CH:14]=[CH:13][C:12]=3[O:11][CH3:10])=[O:25])=[N:52][CH:51]=1

Komponenten

6

Edukt 4

HCID 689584-AminopyrimidineHCID 81531DiisopropylethylamineHCID 2345628-Methoxy-2-oxo-2H-chromene-3-carboxylic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Produkt 1

HCID 866503628-Methoxy-2-oxo-2H-chromene-3-carboxylic acid pyrimidin-4-ylamideAusbeute 11,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

DIEA (0.044 mL, 0.25 mmol) was added to 8-methoxy-3-carboxy-coumarin (0.030 g, 0.14 mmol) and HATU (0.095 g, 0.25 mmol) in 1 mL of dimethylformamide (DMF) with constant stirring at room temperature until a clear solution resulted. Subsequently, pyrimidin-4-ylamine (0.009 g, 0.09 mmol) was added and allowed to react overnight, when a solid precipitated out of solution. The precipitate was filtered and dried under suction and then in vacuo to give 0.003 g of 1541E in an 11% yield: LCMS (ESI) m/z 298 (MH+).

Aufarbeitung

  1. customresulted
  2. customto react overnight
  3. customwhen a solid precipitated out of solution
  4. filtrationThe precipitate was filtered
  5. customdried under suction

Quellen und Nachweise

ORD-Eintrag
ord-2d51c4b1ed764bf48d22b69a4e99b14e
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08642788B2

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