4-Chloro-6-hydrazinylpyrimidine → 2-(6-Chloropyrimidin-4-yl)-4-pyridin-3-yl-1,2-dihydro-3H-pyrazol-3-one

HRID 37898

Reaktionsgleichung

Reaktionsgleichung von HRID 37898
[Cl:1][C:2]1[CH:7]=[C:6]([NH:8][NH2:9])[N:5]=[CH:4][N:3]=1.CN(C)[CH:12]=[C:13]([C:19]1[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=1)[C:14](OCC)=[O:15]>C(O)(=O)C>[Cl:1][C:2]1[N:3]=[CH:4][N:5]=[C:6]([N:8]2[C:14](=[O:15])[C:13]([C:19]3[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=3)=[CH:12][NH:9]2)[CH:7]=1

Komponenten

4

Edukt 2

HCID 2472224-Chloro-6-hydrazinylpyrimidineHCID 687048643-(Dimethylamino)-2-pyridin-3-yl-acrylic acid ethyl ester

Produkt 1

HCID 866723282-(6-Chloropyrimidin-4-yl)-4-pyridin-3-yl-1,2-dihydro-3H-pyrazol-3-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

At RT, 30.0 g (207.5 mmol) of the compound from Example 7A and 50.3 g (228.3 mmol) of the compound from Example 3A are stirred in 1000 ml of glacial acetic acid for 16 h. For work-up, the solvent is removed on a rotary evaporator, the residue is taken up in ethyl acetate and washed with saturated sodium bicarbonate solution until neutral, and the organic phase is concentrated under reduced pressure. The residue is dissolved in 1000 ml of ethanol, 42.8 ml (41.1 g, 228.3 mmol) of 30% strength methanolic sodium methoxide solution are added and the mixture is stirred at RT for 2 h. The reaction mixture is then adjusted to pH 5 using 1 N hydrochloric acid and stirred for 16 h. The precipitate is filtered off, the filter residue is washed with water and ethanol and the product is dried under reduced pressure.

Aufarbeitung

  1. customFor work-up, the solvent is removed on a rotary evaporator
  2. washwashed with saturated sodium bicarbonate solution until neutral, and the organic phase
  3. concentrationis concentrated under reduced pressure
  4. dissolutionThe residue is dissolved in 1000 ml of ethanol
  5. addition42.8 ml (41.1 g, 228.3 mmol) of 30% strength methanolic sodium methoxide solution are added
  6. stirringstirred for 16 h
  7. filtrationThe precipitate is filtered off
  8. washthe filter residue is washed with water and ethanol
  9. customthe product is dried under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-2693a4b649f643509bbdb14e7cf82ccb
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08524699B2

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