Sodium Iodide → (2-chloro-6-phenyl-pyrimidin-4-yl)-(5-methyl-2H-pyrazol-3-yl)-amine

HRID 480631

Reaktionsgleichung

Reaktionsgleichung von HRID 480631
[Cl:1][C:2]1[N:7]=[C:6](Cl)[CH:5]=[C:4]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[N:3]=1.[NH2:15][C:16]1[CH:20]=[C:19]([CH3:21])[NH:18][N:17]=1.C(N(CC)CC)C.[I-].[Na+]>CN(C=O)C>[Cl:1][C:2]1[N:7]=[C:6]([NH:15][C:16]2[NH:17][N:18]=[C:19]([CH3:21])[CH:20]=2)[CH:5]=[C:4]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[N:3]=1

Komponenten

6

Edukt 4

HCID 5238Sodium IodideHCID 8471TriethylamineHCID 931461H-Pyrazol-3-amine, 5-methyl-HCID 2415542,4-Dichloro-6-phenylpyrimidine

Produkt 1

HCID 178418761(2-chloro-6-phenyl-pyrimidin-4-yl)-(5-methyl-2H-pyrazol-3-yl)-amineAusbeute 62,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

To a solution of 2,4-dichloro-6-phenyl-pyrimidine (300 mg, 1.33 mmol) and 3-amino-5-methylpyrazole (129 mg, 1.33 mmol) in DMF (7 mL) is added triethylamine (195 μL, 1.40 mmol) followed by sodium iodide (200 mg, 1.33 mmol) and the reaction mixture is stirred for 15 hours at 90° C. The resulting solution is partitioned between ethyl acetate and water and the organic phase washed with brine, dried over MgSO4 then concentrated in vacuo. The residue is triturated in methanol and the resulting white solid collected by filtration to afford (2-chloro-6-phenyl-pyrimidin-4-yl)-(5-methyl-2H-pyrazol-3-yl)-amine (236 mg, 62%).

Aufarbeitung

  1. customThe resulting solution is partitioned between ethyl acetate and water
  2. washthe organic phase washed with brine
  3. dry with materialdried over MgSO4
  4. concentrationthen concentrated in vacuo
  5. customThe residue is triturated in methanol
  6. filtrationthe resulting white solid collected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-b73ffd7c7f50478aab6098e63cb4d484
Quelldatensatz
uspto-grants-2003_11
Patentnummer
US06653301B2

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