Dimethylformamide → N-(2-fluorophenethyl)-2-(1,3-dimethyl-2,6-dioxo-1,2,3,6-tetrahydropurin-7-yl)acetamide

HRID 1942108

Reaktionsgleichung

Reaktionsgleichung von HRID 1942108
[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].CN(C(ON1N=N[C:28]2[CH:29]=[CH:30][CH:31]=N[C:27]1=2)=[N+](C)C)C.[F:35][P-](F)(F)(F)(F)F.CCO[C:45]([CH3:47])=O.C[N:49]([CH:51]=O)C>>[F:35][C:45]1[CH:47]=[CH:31][CH:30]=[CH:29][C:28]=1[CH2:27][CH2:51][NH:49][C:15](=[O:17])[CH2:14][N:10]1[C:11]2[C:12](=[O:13])[N:1]([CH3:2])[C:3](=[O:4])[N:5]([CH3:6])[C:7]=2[N:8]=[CH:9]1

Komponenten

5

Edukt 4

HCID 6228DimethylformamideHCID 8857Ethyl AcetateHCID 69550AcefyllineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Produkt 1

HCID 28010248N-(2-fluorophenethyl)-2-(1,3-dimethyl-2,6-dioxo-1,2,3,6-tetrahydropurin-7-yl)acetamideAusbeute 31 %

Versuchsvorschrift

Compound 101 (600 mg, 2.5 mmol) was mixed with HATU (1.14 g, 3.0 mmol) in 20 mL of DMF under N2 and stirred at room temperature for 20 min. Compound 117 (0.33 mL, 2.5 mmol) was added. The resulting mixture was stirred overnight. EtOAc (100 mL) was added and the resulting solution was washed with water (3×80 mL) and brine (80 mL), dried over Na2SO4 and filtered. The filtrate was concentrated in vacuo and the resulting solid residue was purified by flash column chromatography on 40 g of silica gel eluting with EtOAc/hexanes. The purified product was triturated with ether (30 mL) and filtered to yield 404 as a white solid (281 mg, 31%). MS (APCI): m/z 360 [M+H]+. Anal. Calcd for C17H18FN5O3.0.3H2O: C, 55.98; H, 5.14; N, 19.20; Found: C, 55.87; H, 5.07; N, 19.13.

Aufarbeitung

  1. stirringThe resulting mixture was stirred overnight
  2. washthe resulting solution was washed with water (3×80 mL) and brine (80 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated in vacuo
  6. customthe resulting solid residue was purified by flash column chromatography on 40 g of silica gel eluting with EtOAc/hexanes
  7. customThe purified product was triturated with ether (30 mL)
  8. filtrationfiltered

Quellen und Nachweise

ORD-Eintrag
ord-c39ae997b67a4fc1a494cd5fb6d05eb7
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08389529B2

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