Methanol → HCID 178493319, Verbindung

HRID 387448

Reaktionsgleichung

Reaktionsgleichung von HRID 387448
[F:1][C:2]([F:23])([F:22])[C:3]1[CH:4]=[C:5]([NH:9][C:10]2[NH:11][C:12]([C:15]3[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=3)=[N:13][N:14]=2)[CH:6]=[CH:7][CH:8]=1.C([O-])([O-])=O.[Cs+].[Cs+].[NH2:30][C:31]1[N:36]=[C:35](Cl)[CH:34]=[C:33]([O:38][CH3:39])[N:32]=1.CO>O1CCOCC1>[CH3:39][O:38][C:33]1[CH:34]=[C:35]([O:21][C:18]2[CH:19]=[CH:20][C:15]([C:12]3[NH:11][C:10]([NH:9][C:5]4[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:22])([F:1])[F:23])[CH:4]=4)=[N:14][N:13]=3)=[CH:16][CH:17]=2)[N:36]=[C:31]([NH2:30])[N:32]=1

Komponenten

6

Edukt 4

HCID 887MethanolHCID 10796Cesium carbonateHCID 798112-Pyrimidinamine, 4-chloro-6-methoxy-HCID 178515914HCID 178515914, Verbindung

Produkt 1

HCID 178493319HCID 178493319, VerbindungAusbeute 40,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

4-(5-{[3-(trifluoromethyl)phenyl]amino}-4H-1,2,4-triazol-3-yl)phenol (100 mg, 0.31 mmol) was dissolved in 3 mL of anhydrous dioxane in 2-5 mL microwave vial (Personal Chemistry). Solid Cs2CO3 (101.7 mg, 0.31 mmol) was added, followed by 2-amino-4-chloro-6-methoxypyrimidine (55.0 mg, 0.34 mmol). The vial was capped and microwaved at 200° C. for 15 min. Then ca. 3 mL of MeOH was added to dissolve the formed suspension. The resulting reddish-brown solution was transferred into a round-bottom flask and solvent was removed in vacuo. The residue was re-dissolved in 3 mL of DMF, filtered through 0.22 u syringe filter and purified by reverse phase preparative HPLC using acetonitrile/water system with 0.01% of TEA. The fractions, containing the product, were collected and partitioned between EtOAc and saturated aqueous NaHCO3. Ethyl acetate layer was washed with brine, dried over anhydrous sodium sulfate and filtered. Solvent was removed in vacuo to give the title compound as an off-white solid (55.6 mg).

Aufarbeitung

  1. customThe vial was capped
  2. custommicrowaved at 200° C. for 15 min
  3. dissolutionto dissolve the formed suspension
  4. customThe resulting reddish-brown solution was transferred into a round-bottom flask
  5. customsolvent was removed in vacuo
  6. dissolutionThe residue was re-dissolved in 3 mL of DMF
  7. filtrationfiltered through 0.22 u syringe
  8. filtrationfilter
  9. custompurified by reverse phase preparative HPLC
  10. additionThe fractions, containing the product
  11. customwere collected
  12. custompartitioned between EtOAc and saturated aqueous NaHCO3
  13. washEthyl acetate layer was washed with brine
  14. dry with materialdried over anhydrous sodium sulfate
  15. filtrationfiltered
  16. customSolvent was removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-276c58e83b464af4a0d4b99842f347c5
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08372971B2

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