Methanol → N-[6-methoxy-5-(2-methoxyphenoxy)-2-(2-pyrimidinyl)-4-pyrimidinyl]-4,4-dimethyl-1-pentanesulfonamide

HRID 397272Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 397272
[H-].[Na+].Cl[C:4]1[N:9]=[C:8]([C:10]2[N:15]=[CH:14][CH:13]=[CH:12][N:11]=2)[N:7]=[C:6]([NH:16][S:17]([CH2:20][CH2:21][CH2:22][C:23]([CH3:26])([CH3:25])[CH3:24])(=[O:19])=[O:18])[C:5]=1[O:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[O:34][CH3:35].[CH3:36][OH:37]>>[CH3:36][O:37][C:4]1[N:9]=[C:8]([C:10]2[N:15]=[CH:14][CH:13]=[CH:12][N:11]=2)[N:7]=[C:6]([NH:16][S:17]([CH2:20][CH2:21][CH2:22][C:23]([CH3:26])([CH3:25])[CH3:24])(=[O:19])=[O:18])[C:5]=1[O:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[O:34][CH3:35]

Komponenten

4

Edukt 3

HCID 887MethanolHCID 24758Sodium hydrideHCID 22999698N-[6-chloro-5-(2-methoxyphenoxy)-2-(2-pyrimidinyl)-4-pyrimidinyl]-4,4-dimethyl-1-pentanesulfonamide

Produkt 1

HCID 22999699N-[6-methoxy-5-(2-methoxyphenoxy)-2-(2-pyrimidinyl)-4-pyrimidinyl]-4,4-dimethyl-1-pentanesulfonamide

Reaktionsbedingungen

Temperatur
105 °C

Versuchsvorschrift

Sodium hydride (60% oil dispersion 354 mg) was cautiously added to a suspension of N-[6-chloro-5-(2-methoxyphenoxy)-2-(2-pyrimidinyl)-4-pyrimidinyl]-4,4-dimethyl-1-pentanesulfonamide (580 mg) in dry methanol (5 ml) in a 10 mm Wheaton reacti-vial™ and the resulting mixture stirred at 105° C. for 4 hours. The reaction was then partitioned between ethyl acetate (20 ml) and 2N aqueous hydrochloric acid (10 ml) and the organic phase separated. The aqueous was extracted with ethyl acetate (20 ml ) and the organic phases combined, washed (water 2×20 ml), dried (Na2SO4) and evaporated under reduced pressure. Column chromatography on silica eluting with a solvent gradient of dichloromethane:methanol 100:0 changing to 98.5:1.5 gave N-[6-methoxy-5-(2-methoxyphenoxy)-2-(2-pyrimidinyl)-4-pyrimidinyl]-4,4-dimethyl-1-pentanesulfonamide as an off-white coloured solid (189 mg).

Aufarbeitung

  1. customThe reaction was then partitioned between ethyl acetate (20 ml) and 2N aqueous hydrochloric acid (10 ml)
  2. customthe organic phase separated
  3. extractionThe aqueous was extracted with ethyl acetate (20 ml )
  4. washwashed (water 2×20 ml)
  5. dry with materialdried (Na2SO4)
  6. customevaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-817519a50f58474ea54b89b6a21cf8de
Quelldatensatz
uspto-grants-2003_08
Patentnummer
US06610518B2

Notizen zur Reaktion

Wird geladen…