Potassium Carbonate → 5-chloro-6-((4-fluorobenzyl)oxy)-3-(5-(2-(2-hydroxypropan-2-yl)pyrimidin-4-yl)-2-methylphenyl)-2-methylpyrimidin-4(3H)-one

HRID 2172600Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2172600
[Cl:1][C:2]1[C:3](=[O:29])[N:4]([C:18]2[CH:23]=[C:22]([C:24](=O)[C:25]#[CH:26])[CH:21]=[CH:20][C:19]=2[CH3:28])[C:5]([CH3:17])=[N:6][C:7]=1[O:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=1.Cl.[OH:31][C:32]([CH3:37])([CH3:36])[C:33]([NH2:35])=[NH:34].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[Cl:1][C:2]1[C:3](=[O:29])[N:4]([C:18]2[CH:23]=[C:22]([C:24]3[CH:25]=[CH:26][N:35]=[C:33]([C:32]([OH:31])([CH3:37])[CH3:36])[N:34]=3)[CH:21]=[CH:20][C:19]=2[CH3:28])[C:5]([CH3:17])=[N:6][C:7]=1[O:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 426142842-Hydroxy-2-methylpropanimidamide hydrochlorideHCID 715826465-chloro-6-(4-fluoro-benzyloxy)-2-methyl-3-(2-methyl-5-propynoyl-phenyl)-3H-pyrimidin-4-one

Produkt 1

HCID 715823355-chloro-6-((4-fluorobenzyl)oxy)-3-(5-(2-(2-hydroxypropan-2-yl)pyrimidin-4-yl)-2-methylphenyl)-2-methylpyrimidin-4(3H)-oneAusbeute 29,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
75 °C

Versuchsvorschrift

To a solution of 5-chloro-6-(4-fluoro-benzyloxy)-2-methyl-3-(2-methyl-5-propynoyl-phenyl)-3H-pyrimidin-4-one of Step C (10 mg, 0.02 mmol) in acetonitrile (1 mL) was added 2-hydroxy-2-methylpropionamidine HCl (5 mg, 0.03 mmol) and potassium carbonate (10 mg, 0.08 mmol) and the slurry was heated at 75° C. for eighteen hours. After cooling to room temperature the reaction was filtered to remove excess salts. The filtrate was concentrated and purified via normal phase chromatography (ethyl acetate/heptane) to provide the title compound as a yellow oil (2.9 mg, 24% yield). MS (M+H): 495

Aufarbeitung

  1. temperatureAfter cooling to room temperature the reaction
  2. filtrationwas filtered
  3. customto remove excess salts
  4. concentrationThe filtrate was concentrated
  5. custompurified via normal phase chromatography (ethyl acetate/heptane)

Quellen und Nachweise

ORD-Eintrag
ord-414ed8fd65af410d9e1a24852356e9a8
Quelldatensatz
uspto-grants-2015_06
Patentnummer
US09056110B2

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