Diisopropylethylamine → 5-Pyrimidinecarboxamide, 4-amino-2-(ethylthio)-N-methoxy-N-methyl-

HRID 1371589Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1371589
[NH2:1][C:2]1[C:7]([C:8]([OH:10])=O)=[CH:6][N:5]=[C:4]([S:11][CH2:12][CH3:13])[N:3]=1.F[P-](F)(F)(F)(F)F.[N:21]1([O:30][C:31](N(C)C)=[N+](C)C)[C:25]2C=CC=CC=2N=N1.O.ON1C2C=CC=CC=2N=N1.C(N(C(C)C)CC)(C)C>CN(C)C=O.C(OCC)(=O)C.O>[CH3:31][O:30][N:21]([CH3:25])[C:8]([C:7]1[C:2]([NH2:1])=[N:3][C:4]([S:11][CH2:12][CH3:13])=[N:5][CH:6]=1)=[O:10]

Komponenten

8

Edukt 4

HCID 81531DiisopropylethylamineHCID 2753004-Amino-2-(ethylthio)pyrimidine-5-carboxylic acidHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 27960291-Hydroxybenzotriazole hydrate

Produkt 1

HCID 119748325-Pyrimidinecarboxamide, 4-amino-2-(ethylthio)-N-methoxy-N-methyl-Ausbeute 98 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 4-amino-2-ethylsulfanyl-pyrimidine-5-carboxylic acid (1.00 g, 5.40 mmol, Sigma) in dimethylformamide were added O-benzotriazol-1-yl-N,N,N′,N′-tetramethyluronium hexafluorophosphate (3.06 g, 8.1 mmol, Aldrich), 1-hydroxy-benzotriazole hydrate (1.09 g, 8.1 mmol, Aldrich) followed by diisopropylethylamine (3.94 g, 29.7 mmol) at 0° C. After stirring for 10–15 minutes, N,O-dimethyl-hydroxylamine. HCl (790 mg, 8.1 mmol, Aldrich) was added. The reaction was stirred at 0° C. to room temperature for 2 hours and then diluted with ethyl acetate and water. The aqueous layer was separated and extracted with ethyl acetate. The combined organic extracts were washed with brine, dried and concentrated. The crude product was purified on silica gel with 1:1 hexane/ethyl acetate to give 4-amino-2-ethylsulfanyl-pyrimidine-5-carboxylic acid methoxy-methyl-amide as a white solid (1.189 g, 98% yield). HRMS, observed: 242.0836; Calcd for M+: 242.0837

Aufarbeitung

  1. stirringThe reaction was stirred at 0° C. to room temperature for 2 hours
  2. customThe aqueous layer was separated
  3. extractionextracted with ethyl acetate
  4. washThe combined organic extracts were washed with brine
  5. customdried
  6. concentrationconcentrated
  7. customThe crude product was purified on silica gel with 1:1 hexane/ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-2dd3dcd57cee4c9fa34772f908800208
Quelldatensatz
uspto-grants-2007_01
Patentnummer
US07157455B2

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