Cesium carbonate → 5-[5-(4-Methoxy-phenyl)-pyrimidin-2-ylamino]-pyridine-2-carboxylic acid methyl ester

HRID 2065566Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2065566
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([O:10][CH3:11])=[O:9])=[N:6][CH:7]=1.Cl[C:13]1[N:18]=[CH:17][C:16]([C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=2)=[CH:15][N:14]=1.CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.C([O-])([O-])=O.[Cs+].[Cs+]>CC([O-])=O.CC([O-])=O.[Pd+2].O1CCOCC1>[CH3:11][O:10][C:8]([C:5]1[CH:4]=[CH:3][C:2]([NH:1][C:13]2[N:14]=[CH:15][C:16]([C:19]3[CH:20]=[CH:21][C:22]([O:25][CH3:26])=[CH:23][CH:24]=3)=[CH:17][N:18]=2)=[CH:7][N:6]=1)=[O:9]

Komponenten

7

Edukt 4

HCID 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 27610202-Chloro-5-(4-methoxyphenyl)pyrimidineHCID 12457877Methyl 5-aminopyridine-2-carboxylate

Produkt 1

HCID 673658245-[5-(4-Methoxy-phenyl)-pyrimidin-2-ylamino]-pyridine-2-carboxylic acid methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

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

Reaktionsbedingungen

Temperatur
130 °C

Versuchsvorschrift

A vial is charged with methyl 5-aminopicolinate 2 (0.83 mmol), 2-chloro-5-(4-methoxy-phenyl)-pyrimidine 3 (0.83 mmol), Pd(OAc)2 (0.124 mmol), xanthphos (0.124 mmol), Cs2CO3 (0.83 mmol) and anhydrous 1,4-dioxane (5 mL). The vial is evacuated and refilled with N2 twice and the mixture is heated in a microwave oven at 130° C. for 20 min. The vial is cooled to it and the reaction mixture is diluted with DCM, washed with 10% NH4Cl solution, brine and dried over Na2SO4. The solvent is removed in vacuum and the crude is triturated with EtOAc to afford 5-[5-(4-methoxy-phenyl)-pyrimidin-2-ylamino]-pyridine-2-carboxylic acid methyl ester 4 as light brown solid. NMR (400 MHz, d6-DMSO) δ 10.62 (s, 1H), 8.93 (s, 2H), 8.83 (bs, 1H), 8.46 (d, J=8.0 Hz, 1H), 8.27 (d, J=8.0 Hz, 1H), 7.72-7.70 (m, 2H), 7.08-7.06 (m, 2H), 3.86 (s, 3H), 3.81 (s, 3H). MS (m/z) (M+1)+: 337.1.

Aufarbeitung

  1. customThe vial is evacuated
  2. additionrefilled with N2 twice
  3. temperatureThe vial is cooled to it
  4. additionthe reaction mixture is diluted with DCM
  5. washwashed with 10% NH4Cl solution, brine
  6. dry with materialdried over Na2SO4
  7. customThe solvent is removed in vacuum
  8. customthe crude is triturated with EtOAc

Quellen und Nachweise

ORD-Eintrag
ord-f23b0726829f4bc1b6700a4c98d72af2
Quelldatensatz
uspto-grants-2012_10
Patentnummer
US08288540B2

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