Cesium carbonate → 5-Bromo-3-(1-cyclopropyl-1H-pyrazol-4-ylamino)-1-methylpyrazin-2(1H)-one

HRID 1918822Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1918822
[CH:1]1([N:4]2[CH:8]=[C:7]([NH2:9])[CH:6]=[N:5]2)[CH2:3][CH2:2]1.Br[C:11]1[C:12](=[O:19])[N:13]([CH3:18])[CH:14]=[C:15]([Br:17])[N:16]=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+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C(Cl)Cl.O1CCOCC1>[Br:17][C:15]1[N:16]=[C:11]([NH:9][C:7]2[CH:6]=[N:5][N:4]([CH:1]3[CH2:3][CH2:2]3)[CH:8]=2)[C:12](=[O:19])[N:13]([CH3:18])[CH:14]=1

Komponenten

8

Edukt 4

HCID 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 130629693,5-Dibromo-1-methyl-1H-pyrazin-2-oneHCID 510003781-Cyclopropyl-1H-pyrazol-4-amine

Produkt 1

HCID 580442185-Bromo-3-(1-cyclopropyl-1H-pyrazol-4-ylamino)-1-methylpyrazin-2(1H)-one

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 6344DichloromethaneLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a seal tube equipped with a stirring bar, 1-cyclopropyl-1H-pyrazol-4-amine (600 mg, 4.87 mmol), 3,5-dibromo-1-methylpyrazin-2(1H)-one (1.96 g, 7.31 mmol), Pd2(dba)3 (223.1 mg, 0.244 mmol), XantPhos (225.5 mg, 0.390 mmol), Cs2CO3 (5.25 g, 16.08 mmol) and dioxane (12 mL) were added. The tube was sealed and heated at 100° C. overnight. CH2Cl2 (200 mL) was added to the resulting mixture, and the CH2Cl2 solution was washed with water (30 mL×3). The precipitate in the aqueous phase was filtered as pure product 114b. The organic phase was dried over MgSO4, filtered and solvent removed in vacuo. CH2Cl2/ether (1:2, 3 mL) were added to the residue and the mixture was sonicated. The precipitate was filtered, combined with the filtered solids from the aqueous phase, and dried. 5-Bromo-3-(1-cyclopropyl-1H-pyrazol-4-ylamino)-1-methylpyrazin-2(1H)-one 114b was obtained as a yellow solid.

Aufarbeitung

  1. customTo a seal tube equipped with a stirring bar
  2. customThe tube was sealed
  3. washthe CH2Cl2 solution was washed with water (30 mL×3)
  4. filtrationThe precipitate in the aqueous phase was filtered as pure product 114b
  5. dry with materialThe organic phase was dried over MgSO4
  6. filtrationfiltered
  7. customsolvent removed in vacuo
  8. additionCH2Cl2/ether (1:2, 3 mL) were added to the residue
  9. customthe mixture was sonicated
  10. filtrationThe precipitate was filtered
  11. customdried

Quellen und Nachweise

ORD-Eintrag
ord-fcbd57cb81a241cab9dd60b564ffe735
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08618107B2

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