Cesium carbonate → N4-Methyl-N2-(4-(4-methyl-1H-imidazol-1-yl)phenyl)-6-((2,2,2-trifluoroethoxy)methyl)-pyrimidine-2,4-diamine

HRID 59133

Reaktionsgleichung

Reaktionsgleichung von HRID 59133
Cl[C:2]1[N:7]=[C:6]([NH:8][CH3:9])[CH:5]=[C:4]([CH2:10][O:11][CH2:12][C:13]([F:16])([F:15])[F:14])[N:3]=1.[CH3:17][C:18]1[N:19]=[CH:20][N:21]([C:23]2[CH:29]=[CH:28][C:26]([NH2:27])=[CH:25][CH:24]=2)[CH:22]=1.C(=O)([O-])[O-].[Cs+].[Cs+].C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2)CCCCC1>O1CCOCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:9][NH:8][C:6]1[CH:5]=[C:4]([CH2:10][O:11][CH2:12][C:13]([F:16])([F:15])[F:14])[N:3]=[C:2]([NH:27][C:26]2[CH:25]=[CH:24][C:23]([N:21]3[CH:22]=[C:18]([CH3:17])[N:19]=[CH:20]3)=[CH:29][CH:28]=2)[N:7]=1

Komponenten

7

Edukt 4

HCID 10796Cesium carbonateHCID 27342162-(Dicyclohexylphosphino)biphenylHCID 160051704-(4-Methyl-1h-imidazol-1-yl)benzenamineHCID 1178212102-Chloro-N-methyl-6-((2,2,2-trifluoroethoxy)methyl)pyrimidin-4-amine

Produkt 1

HCID 86344431N4-Methyl-N2-(4-(4-methyl-1H-imidazol-1-yl)phenyl)-6-((2,2,2-trifluoroethoxy)methyl)-pyrimidine-2,4-diamineAusbeute 40,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 167845palladium(II) acetateKatalysatorHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

A mixture of 2-chloro-N-methyl-6-((2,2,2-trifluoroethoxy)methyl)pyrimidin-4-amine (85 mg, 0.33 mmol), 4-(4-methyl-1H-imidazol-1-yl)aniline (100 mg, 0.58 mmol), cesium carbonate (217 mg, 0.67 mmol), palladium(II) acetate (11 mg, 0.05 mmol) and 2-(dicyclohexylphosphino)-biphenyl (17 mg, 0.05 mmol) in dioxane (3 mL) was heated in a microwave reactor under notrogen atmosphere at 120° C. for 90 min. The reaction mixture was filtered through a pad of diatomeous earth which was eluted with MeOH. The mixture was partitioned between EtOAc and sodium hydroxide (aq, 1 M). The organic phase was separated, dried over sodium sulfate and concentrated in vacuum. The residue was purified by preparative HPLC to give the title compound as a solid 52 mg, (40%).

Aufarbeitung

  1. filtrationThe reaction mixture was filtered through a pad of diatomeous earth which
  2. washwas eluted with MeOH
  3. customThe mixture was partitioned between EtOAc and sodium hydroxide (aq, 1 M)
  4. customThe organic phase was separated
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuum
  7. customThe residue was purified by preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-5b10546332b64f55a15b362357df6f61
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09439904B2

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