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Sodium Carbonate → 5-(2-methyl-3,6-dihydro-2H-pyran-4-yl)pyrazin-2-amine

HRID 595840
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 595840
FC(F)(F)S(O[C:7]1[CH2:8][CH:9]([CH3:13])[O:10][CH2:11][CH:12]=1)(=O)=O.CC1(C)C(C)(C)OB([C:24]2[N:25]=[CH:26][C:27]([NH2:30])=[N:28][CH:29]=2)O1.C([O-])([O-])=O.[Na+].[Na+]>COCCOC.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C(Cl)Cl>[CH3:13][CH:9]1[CH2:8][C:7]([C:24]2[N:25]=[CH:26][C:27]([NH2:30])=[N:28][CH:29]=2)=[CH:12][CH2:11][O:10]1
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Komponenten

6

Edukt 3

HCID 10340Sodium CarbonateHCID 179989875-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyrazin-2-amineHCID 1180454962-methyl-3,6-dihydro-2H-pyran-4-yl trifluoromethanesulfonate

Produkt 1

HCID 1180453955-(2-methyl-3,6-dihydro-2H-pyran-4-yl)pyrazin-2-amineAusbeute 45,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418807
HCID 178418807, Verbindung
Katalysator
HCID 80711,2-DimethoxyethaneLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

To a solution of 2-methyl-3,6-dihydro-2H-pyran-4-yl trifluoromethanesulfonate (0.637 g, 2.88 mmol), 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrazin-2-amine (0.914 g, 3.74 mmol), and PdCl2(dppf)-CH2Cl2 adduct (0.235 g, 0.288 mmol) in DME (9.82 mL) was added 2M Na2CO3 (3.27 mL). The reaction mixture was heated at microwave synthesizer (120° C., 10 min). Ethyl acetated was added, and washed with sat NaHCO3, and water. Then the desired compound was extracted to 1N HCl aqueous layer, and washed with EtOAc. Basified with 2N NaOH, and the product was extracted to EtOAc layer. EtOAc organic layer was washed with water and dried over Na2SO4. Filtered and concentrated to provide 250 mg of desired compound. LCMS (m/z): 192.2 (MH+), 0.40 min.

Aufarbeitung

  1. additionEthyl acetated was added
  2. washwashed
  3. extractionThen the desired compound was extracted to 1N HCl aqueous layer
  4. washwashed with EtOAc
  5. extractionBasified with 2N NaOH, and the product was extracted to EtOAc layer
  6. washEtOAc organic layer was washed with water
  7. dry with materialdried over Na2SO4
  8. filtrationFiltered
  9. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-e82ed1e6ea9e4fdd8a2f4778c27de53b
Quelldatensatz
uspto-grants-2016_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09242996B2

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