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Methanol → N-[6-methoxy-5-(2-methoxyphenoxy)-2-(2-pyrimidinyl)-4-pyrimidinyl]-3,3-dimethyl-1-butanesulfonamide

HRID 397270
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 397270
[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][C:22]([CH3:25])([CH3:24])[CH3:23])(=[O:19])=[O:18])[C:5]=1[O:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[O:33][CH3:34].[CH3:35][OH:36]>>[CH3:35][O:36][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][C:22]([CH3:25])([CH3:24])[CH3:23])(=[O:19])=[O:18])[C:5]=1[O:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[O:33][CH3:34]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 3

HCID 887MethanolHCID 24758Sodium hydrideHCID 22999716N-[6-chloro-5-(2-methoxyphenoxy)-2-(2-pyrimidinyl)-4-pyrimidinyl]-3,3-dimethyl-1-butanesulfonamide

Produkt 1

HCID 22999702N-[6-methoxy-5-(2-methoxyphenoxy)-2-(2-pyrimidinyl)-4-pyrimidinyl]-3,3-dimethyl-1-butanesulfonamide

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

Sodium hydride (80% oil dispersion 132 mg) was cautiously added to a suspension of N-[6-chloro-5-(2-methoxyphenoxy)-2-(2-pyrimidinyl)-4-pyrimidinyl]-3,3-dimethyl-1-butanesulfonamide (Preparation 2)(420 mg) in dry methanol (12 ml) divided equally between two 10 ml Wheaton reacti-vials™, and the resulting mixtures stirred at 100° C. for 3 hours. The reactions were then combined and partitioned between ethyl acetate (40 ml) and 2N aqueous hydrochloric acid (20 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 99:1 changing to 97:3 gave N-[6-methoxy-5-(2-methoxyphenoxy)-2-(2-pyrimidinyl)-4-pyrimidinyl]-3,3-dimethyl-1-butanesulfonamide as an off-white coloured foam (265 mg).

Aufarbeitung

  1. custompartitioned between ethyl acetate (40 ml) and 2N aqueous hydrochloric acid (20 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-564d4e638a304322830c6488df1d1f5b
Quelldatensatz
uspto-grants-2003_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06610518B2

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