Sodium Carbonate → 5-(3-Chloropyridin-4-yl)-N4-cyclopentylpyrimidine-2,4-diamine

HRID 79105

Reaktionsgleichung

Reaktionsgleichung von HRID 79105
Br[C:2]1[C:3]([NH:9][CH:10]2[CH2:14][CH2:13][CH2:12][CH2:11]2)=[N:4][C:5]([NH2:8])=[N:6][CH:7]=1.[Cl:15][C:16]1[CH:17]=[N:18][CH:19]=[CH:20][C:21]=1B(O)O.C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Cl:15][C:16]1[CH:17]=[N:18][CH:19]=[CH:20][C:21]=1[C:2]1[C:3]([NH:9][CH:10]2[CH2:14][CH2:13][CH2:12][CH2:11]2)=[N:4][C:5]([NH2:8])=[N:6][CH:7]=1

Komponenten

6

Edukt 3

HCID 10340Sodium CarbonateHCID 38618773-Chloro-4-pyridineboronic acidHCID 582998155-Bromo-N4-cyclopentylpyrimidine-2,4-diamine

Produkt 1

HCID 582995755-(3-Chloropyridin-4-yl)-N4-cyclopentylpyrimidine-2,4-diamineAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418476HCID 178418476, VerbindungKatalysatorHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

To a solution of 2 (2.57 g, 10.0 mmol) in dioxane (75 mL) were added 3-chloropyridine-4-boronic acid (4.72 g, 10.0 mmol), trans-dichlorobis(triphenylphosphine)-palladium(II) (702 mg, 1.0 mmol), and sodium carbonate (3.82 g, 36 mmol, in 36 mL of water). The mixture thus obtained was purged with N2 for 10 min and heated at 120° C. in a sealed tube for 22 h. The reaction mixture was diluted with water and the product was extracted with chloroform. The organic layers were dried (MgSO4) and concentrated. The residue was purified by flash chromatography on silica gel eluting with 2.5% methanol in dichloromethane to give the title compound (3) as a white solid (2.31 g, 80%). 1H NMR (500 MHz, DMSO-d6) δ 8.64 (1H, s), 8.50 (1H, d, J=4.9 Hz), 7.51 (1H, s), 7.34 (1H, d, 1H, J=4.9 Hz), 6.21 (2H, d, 1H, br s), 5.97 (1H, d, J =7.6 Hz), 4.43 (1H, p, J=7.4 Hz), 1.84 (2H, m), 1.62 (2H, m), 1.40-1.49 (4H, m) ppm; LCMS-ESI (POS), M/Z, M+1: Found 290.0, Calculated 290.1.

Aufarbeitung

  1. customThe mixture thus obtained
  2. customwas purged with N2 for 10 min
  3. additionThe reaction mixture was diluted with water
  4. extractionthe product was extracted with chloroform
  5. dry with materialThe organic layers were dried (MgSO4)
  6. concentrationconcentrated
  7. customThe residue was purified by flash chromatography on silica gel eluting with 2.5% methanol in dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-88396905ce1249689de6609c56c357c3
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08841312B2

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