Triphenylphosphine → Tert-butyl 2-[4-(2-aminopyrimidin-5-yl)-2-fluorophenoxy]propionate

HRID 500151Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 500151
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O.[OH:32][C@@H:33]([CH3:41])[C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35].[NH2:42][C:43]1[N:48]=[CH:47][C:46]([C:49]2[CH:54]=[CH:53][C:52](O)=[C:51]([F:56])[CH:50]=2)=[CH:45][N:44]=1>O1CCCC1>[NH2:42][C:43]1[N:48]=[CH:47][C:46]([C:49]2[CH:54]=[CH:53][C:52]([O:32][CH:33]([CH3:41])[C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])=[C:51]([F:56])[CH:50]=2)=[CH:45][N:44]=1

Komponenten

6

Edukt 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 129438461,1-Dimethylethyl (2S)-2-hydroxypropanoateHCID 672239574-(2-Aminopyrimidin-5-yl)-2-fluorophenol

Produkt 1

HCID 67223953Tert-butyl 2-[4-(2-aminopyrimidin-5-yl)-2-fluorophenoxy]propionateAusbeute 72 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of triphenylphosphine (0.315 g, 1.2 mmol) in tetrahydrofuran (THF, 5.0 mL) was added diethyl azodicarboxylate (0.19 mL, 1.2 mmol) and tert-butyl(S)-2-hydroxypropanoate (292 mg, 2 mmol) followed by 4-(2-aminopyrimidin-5-yl)-2-fluorophenol (0.20 g, 1.0 mmol) at RT (RT) under nitrogen. The mixture was stirred overnight at RT, evaporated and the residue was purified by chromatography on silica gel to afford the desired product (0.24 g, 72%). LCMS: (M+H)=334. 1.

Aufarbeitung

  1. custom(RT)
  2. customevaporated
  3. customthe residue was purified by chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-1d771913e51a4000b228ef7ef2ffbe09
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07767675B2

Notizen zur Reaktion

Wird geladen…