1,2-Dichloroethane → 4-Chloro-6,7-dimethoxyquinazoline
Reaktionsgleichung
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][N:7]=[C:6]2O.C(NC(C)C)(C)C.[Cl:23]CCCl>>[Cl:23][C:6]1[C:5]2[C:10](=[CH:11][C:12]([O:13][CH3:14])=[C:3]([O:2][CH3:1])[CH:4]=2)[N:9]=[CH:8][N:7]=1Komponenten
Reaktionsbedingungen
- Temperatur
- 80 °C
Versuchsvorschrift
To a suspension of 6,7-Dimethoxy-quinazolin-4-ol (1.65 g, 8.0 mmol) and phosporousoxychloride (1.52 ml, 16.4 mmol) in 1,2-dichloroethane (16 ml) was added diisopropylamine (3.48 ml, 20 mmol) in a dropwise fashion. The mixture was then heated to 80° C. under an inert atmosphere for 16 hours. After this time the reaction was cooled to room temperature and concentrated in vacuo to dryness, dissolved in CH2Cl2 (50 ml) and washed with sodium bicarbonate solution (5% aqueous, 2*25 ml). The organic layer was separated, dried using MgSO4, filtered and concentrated in vacuo to give a brown residue that was purified by flash chromatography (SiO2) eluted with CH2Cl2:EtOAc—2:98 then 5:95 to give the title compound (1.6 g, 88.9%) as a yellow solid. m/z (LC-MS, ESP): 207 [M+H]+, R/T=3.51 mins
Aufarbeitung
- temperatureAfter this time the reaction was cooled to room temperature
- concentrationconcentrated in vacuo to dryness
- dissolutiondissolved in CH2Cl2 (50 ml)
- washwashed with sodium bicarbonate solution (5% aqueous, 2*25 ml)
- customThe organic layer was separated
- customdried
- filtrationfiltered
- concentrationconcentrated in vacuo
- customto give a brown residue that
- customwas purified by flash chromatography (SiO2)
- washeluted with CH2Cl2
Quellen und Nachweise
- ORD-Eintrag
- ord-ee1961e04388462793459e5e4568c33e
- Quelldatensatz
- uspto-grants-2009_03
- Patentnummer
- US07504397B2
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