2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → Methyl 5-methyl-2-phenyl-7-p-tolylpyrazolo[1,5-a]pyrimidine-6-carboxylate

HRID 472814Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 472814
[CH3:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][CH:3]=1.[C:10]1([C:16]2[CH:20]=[C:19]([NH2:21])[NH:18][N:17]=2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.O=[C:23]([CH3:29])[CH2:24][C:25]([O:27][CH3:28])=[O:26].C(C1C(=O)C(Cl)=C(Cl)C(=O)C=1C#N)#N>C1COCC1.CCCCCCC.N1CCCCC1>[CH3:29][C:23]1[C:24]([C:25]([O:27][CH3:28])=[O:26])=[C:6]([C:5]2[CH:8]=[CH:9][C:2]([CH3:1])=[CH:3][CH:4]=2)[N:18]2[N:17]=[C:16]([C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH:20]=[C:19]2[N:21]=1

Komponenten

8

Edukt 4

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 77254-MethylbenzaldehydeHCID 7757Methyl acetoacetateHCID 1366553-Amino-5-phenylpyrazole

Produkt 1

HCID 66693154Methyl 5-methyl-2-phenyl-7-p-tolylpyrazolo[1,5-a]pyrimidine-6-carboxylateAusbeute 64,4 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 8082PiperidineKatalysatorHCID 8028TetrahydrofuranLösungsmittelHCID 8900HeptaneLösungsmittel

Versuchsvorschrift

To a stirred solution of 4-methylbenzaldehyde (1.2 g, 9.99 mmol), 3-phenyl-1H-pyrazol-5-amine (1.6 g, 9.99 mmol), and methyl 3-oxobutanoate (1.3 g, 10.99 mmol) in THF (80 mL) and heptane (20 mL) was added piperidine (30 mL, 0.303 mmol). The reaction mixture was heated at reflux for 20 h. The solvent was evaporated and the crude material was dissolved in CH2Cl2. DDQ (2041 mg, 8.99 mmol) was added and the mixture was stirred at room temperature for 1 h. The solvent was evaporated. Purification by silica gel chromatography provided the title compound (2.3 g, 64.4%). 1H-NMR (500 MHz, CDCl3) δ ppm 2.47 (3H, s), 2.65 (3H, s), 3.64 (3H, s), 6.93 (1H, s), 7.31-7.47 (5H, m), 7.63 (2H, d, J=7.9 Hz), 7.86-7.99 (2H, m).

Aufarbeitung

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 20 h
  3. customThe solvent was evaporated
  4. dissolutionthe crude material was dissolved in CH2Cl2
  5. customThe solvent was evaporated
  6. customPurification by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-f588f73abd2849428bb8829abd107e9a
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08633200B2

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