Reaktionsgleichung
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[C:9]1[N:14]=[C:13]([O:15]C)[C:12]([CH2:17][O:18][C:19]2[CH:24]=[C:23]([CH:25]([CH3:27])[CH3:26])[CH:22]=[CH:21][C:20]=2[CH3:28])=[C:11]([CH3:29])[N:10]=1.Cl>>[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[C:9]1[N:14]=[C:13]([OH:15])[C:12]([CH2:17][O:18][C:19]2[CH:24]=[C:23]([CH:25]([CH3:26])[CH3:27])[CH:22]=[CH:21][C:20]=2[CH3:28])=[C:11]([CH3:29])[N:10]=1Komponenten
Reaktionsbedingungen
- Temperatur
- 100 °C
Versuchsvorschrift
A mixture of 2-(2,6-dimethylphenyl)-5-[(5-isopropyl-2-methylphenoxy)methyl]-4-methoxy-6-methylpyrimidine (1.29 g, 3.30 mmol) and 6 N HCl is heated at 100° C. for 3 h (until starting material is consumed as determined by LC/MS analysis). The resulting mixture is adjusted to pH 6 using 10 N NaOH and extracted with EtOAc (100 mL×3). The combined extracts are washed with brine (50 mL), dried over anhydrous sodium sulfate, filtered and evaporated at reduced pressure to obtain a yellow gum. Purification by chromatography on silica gel (50-100% EtOAc/Hexanes) provides the title compound as a white solid. 1H NMR (400 MHz, CDCl3) δ 11.4 (br s, 1H), 6.75-7.26 (m, 6H), 5.00 (s, 2H), 2.86 (m, 1H), 2.51 (s, 3H), 2.22 (s, 6H), 2.19 (s, 3H), 1.24 (d, J=6.8 Hz, 6H); LC-MS found 377.4 (MH+), rt=2.87 min, Method 3.
Aufarbeitung
- custom(until starting material is consumed as determined by LC/MS analysis)
- extractionextracted with EtOAc (100 mL×3)
- washThe combined extracts are washed with brine (50 mL)
- dry with materialdried over anhydrous sodium sulfate
- filtrationfiltered
- customevaporated at reduced pressure
- customto obtain a yellow gum
- customPurification by chromatography on silica gel (50-100% EtOAc/Hexanes)
Quellen und Nachweise
- ORD-Eintrag
- ord-a6ced49924f74e068ebc9141d1c47c9c
- Quelldatensatz
- uspto-grants-2012_03
- Patentnummer
- US08129395B2
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