Potassium Carbonate → 1-(6-(2-Butynyloxy)pyrimidin-4-yl)-cis-2,6-dimethylhexahydroazepine

HRID 2069893

Reaktionsgleichung

Reaktionsgleichung von HRID 2069893
F[C:2]1[CH:7]=[C:6](F)[N:5]=[CH:4][N:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:15]([OH:19])[C:16]#[C:17][CH3:18].[CH3:20][C@H:21]1[CH2:27][CH2:26][CH2:25][C@@H:24]([CH3:28])[CH2:23][NH:22]1>O.C1(C)C=CC=CC=1.C(N(CC)CC)C>[CH2:15]([O:19][C:6]1[N:5]=[CH:4][N:3]=[C:2]([N:22]2[CH2:23][C@H:24]([CH3:28])[CH2:25][CH2:26][CH2:27][C@@H:21]2[CH3:20])[CH:7]=1)[C:16]#[C:17][CH3:18]

Komponenten

8

Edukt 4

HCID 11430Potassium CarbonateHCID 129912-Butyn-1-olHCID 1377174,6-DifluoropyrimidineHCID 66594949cis-2,6-Dimethylhexahydroazepine

Produkt 1

HCID 665949551-(6-(2-Butynyloxy)pyrimidin-4-yl)-cis-2,6-dimethylhexahydroazepine

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittelHCID 8471TriethylamineLösungsmittel

Reaktionsbedingungen

Temperatur
30 °C

Versuchsvorschrift

To a mixture obtained by adding 110.0 g of 4,6-difluoropyrimidine, 132.3 g of potassium carbonate and 19.2 g of triethylamine to 220.0 g of toluene, 69.8 g of 2-butyn-1-ol is added dropwise at 25 to 30° C. over one hour, followed by stirring at 30° C. Then, 220.0 g of water is added dropwise into the reaction mixture, followed by stirring. Then, 126.6 g of cis-2,6-dimethylhexahydroazepine is added dropwise and, after the mixture is stirred at 30° C., the reaction mixture is allowed to stand. After separating into the organic layer and the aqueous layer, the aqueous layer is removed and the organic layer is washed once with 220.0 g of 5% hydrochloric acid and then washed once with 220.0 g of water. The organic layer is concentrated to obtain 1-(6-(2-butynyloxy)pyrimidin-4-yl)-cis-2,6-dimethylhexahydroazepine (hereinafter referred to as the present compound (4)).

Aufarbeitung

  1. customTo a mixture obtained
  2. additionis added dropwise at 25 to 30° C. over one hour
  3. stirringby stirring
  4. stirringafter the mixture is stirred at 30° C.
  5. customAfter separating into the organic layer
  6. customthe aqueous layer, the aqueous layer is removed
  7. washthe organic layer is washed once with 220.0 g of 5% hydrochloric acid
  8. washwashed once with 220.0 g of water
  9. concentrationThe organic layer is concentrated

Quellen und Nachweise

ORD-Eintrag
ord-be5bc849d89a4e97890072fc0fcff32a
Quelldatensatz
uspto-grants-2012_10
Patentnummer
US08299245B2

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