Lithium iodide → Bms-707035

HRID 720280Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 720280
[F:1][C:2]1[CH:29]=[CH:28][C:5]([CH2:6][NH:7][C:8]([C:10]2[N:11]=[C:12]([N:20]3[CH2:25][CH2:24][CH2:23][CH2:22][S:21]3(=[O:27])=[O:26])[N:13]([CH3:19])[C:14](=[O:18])[C:15]=2[O:16]C)=[O:9])=[CH:4][CH:3]=1.[I-].[Li+]>N1C(C)=CC(C)=CC=1C>[F:1][C:2]1[CH:29]=[CH:28][C:5]([CH2:6][NH:7][C:8]([C:10]2[N:11]=[C:12]([N:20]3[CH2:25][CH2:24][CH2:23][CH2:22][S:21]3(=[O:27])=[O:26])[N:13]([CH3:19])[C:14](=[O:18])[C:15]=2[OH:16])=[O:9])=[CH:4][CH:3]=1

Komponenten

4

Edukt 2

HCID 66321Lithium iodideHCID 58739064HCID 58739064, Verbindung

Produkt 1

HCID 54682040Bms-707035Ausbeute 52,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 79532,4,6-TrimethylpyridineLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

A mixture of 2-(1,1-dioxo-1λ6-[1,2]thiazinan-2-yl)-5-methoxy-1-methyl-6-oxo-1,6-dihydro-pyrimidine-4-carboxylic acid 4-fluoro-benzylamide (0.115 g, 0.27 mmol) in 2,4,6-collidine (3 ml) was treated with lithium iodide (0.060 g) and the resulting mixture was heated at 120° C. for 30 min. The collidine was then evaporated in vacuo, the residue was diluted with a small volume of water and the pH was adjusted to a value of 7 with 0.1 N hydrochloric acid. The aqueous phase was extracted three times with dichloromethane and the combined organic extracts were washed with brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by chromatography on reversed phase silica gel (Waters, C-18, 125 A, elution with water-acetonitrile 7:3 to 6:4) to give 0.058 g (52% yield) of the title amide as a white solid; mp 226–227° C. (dichloromethane-ethanol).

Aufarbeitung

  1. customThe collidine was then evaporated in vacuo
  2. additionthe residue was diluted with a small volume of water
  3. extractionThe aqueous phase was extracted three times with dichloromethane
  4. washthe combined organic extracts were washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by chromatography on reversed phase silica gel (Waters, C-18, 125 A,
  8. washelution with water-acetonitrile 7:3 to 6:4)

Quellen und Nachweise

ORD-Eintrag
ord-eb23988a48954a929563fb78fd4aac3c
Quelldatensatz
uspto-grants-2006_11
Patentnummer
US07135467B2

Notizen zur Reaktion

Wird geladen…