Dimethylacetamide → 6-{[3-chloro-5-(2,2-diethoxyethoxy)pyridin-2-yl]oxy}-N-(5-methylpyrazin-2-yl)quinazoline-4-amine

HRID 1517284

Reaktionsgleichung

Reaktionsgleichung von HRID 1517284
[Cl:1][C:2]1[C:3](F)=[N:4][CH:5]=[C:6]([O:8][CH2:9][CH:10]([O:14][CH2:15][CH3:16])[O:11][CH2:12][CH3:13])[CH:7]=1.CC(C)([O-])C.[K+].CN(C)C(=O)C.[CH3:30][C:31]1[N:32]=[CH:33][C:34]([NH:37][C:38]2[C:47]3[C:42](=[CH:43][CH:44]=[C:45]([OH:48])[CH:46]=3)[N:41]=[CH:40][N:39]=2)=[N:35][CH:36]=1>C(Cl)(Cl)Cl>[Cl:1][C:2]1[C:3]([O:48][C:45]2[CH:46]=[C:47]3[C:42](=[CH:43][CH:44]=2)[N:41]=[CH:40][N:39]=[C:38]3[NH:37][C:34]2[CH:33]=[N:32][C:31]([CH3:30])=[CH:36][N:35]=2)=[N:4][CH:5]=[C:6]([O:8][CH2:9][CH:10]([O:14][CH2:15][CH3:16])[O:11][CH2:12][CH3:13])[CH:7]=1

Komponenten

6

Edukt 4

HCID 31374DimethylacetamideHCID 23665647Potassium tert-butoxideHCID 684276023-Chloro-5-(2,2-diethoxyethoxy)-2-fluoropyridineHCID 1356182224-((5-Methylpyrazin-2-yl)amino)quinazolin-6-ol

Produkt 1

HCID 684277516-{[3-chloro-5-(2,2-diethoxyethoxy)pyridin-2-yl]oxy}-N-(5-methylpyrazin-2-yl)quinazoline-4-amineAusbeute 53 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Versuchsvorschrift

3-Chloro-5-(2,2-diethoxyethoxy)-2-fluoropyridine (460 mg, 1.74 mmol) and potassium tert-butoxide (160 mg, 1.4 mmol) were added to an N,N-dimethylacetamide suspension (0.9 ml) of 4-[(5-methylpyrazin-2-yl)amino]quinazolin-6-ol (180 mg, 0.71 mmol), and reacted under a nitrogen atmosphere at 200° C. for 30 minutes, using microwaves. The reaction solution was cooled to room temperature, then diluted with chloroform. The organic layer was washed with water and saturated saline water, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (chloroform:methanol=96:4) and amine-type silica gel column chromatography (hexane:ethyl acetate=50:50) to obtain 6-{[3-chloro-5-(2,2-diethoxyethoxy)pyridin-2-yl]oxy}-N-(5-methylpyrazin-2-yl)quinazoline-4-amine (187 mg, yield: 53%) as a pale yellow solid.

Aufarbeitung

  1. customreacted under a nitrogen atmosphere at 200° C. for 30 minutes
  2. washThe organic layer was washed with water and saturated saline water
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (chloroform:methanol=96:4) and amine-type silica gel column chromatography (hexane:ethyl acetate=50:50)

Quellen und Nachweise

ORD-Eintrag
ord-11d54122ab054e30be33a166e908f3bf
Quelldatensatz
uspto-grants-2012_07
Patentnummer
US08232284B2

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