Trichloroisocyanuric Acid → {5-Chloro-4-[2-(4-fluorophenyl)-8-methylimidazo[1,2-a]pyrazin-3-yl]-pyrimidin-2-yl}-cyclopropylamine

HRID 2233116Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2233116
[Cl:1]N1C(=O)N(Cl)C(=O)N(Cl)C1=O.[CH:13]1([NH:16][C:17]2[N:22]=[C:21]([C:23]3[N:27]4[CH:28]=[CH:29][N:30]=[C:31]([CH3:32])[C:26]4=[N:25][C:24]=3[C:33]3[CH:38]=[CH:37][C:36]([F:39])=[CH:35][CH:34]=3)[CH:20]=[CH:19][N:18]=2)[CH2:15][CH2:14]1>C(Cl)(Cl)Cl.C(Cl)Cl>[Cl:1][C:20]1[C:21]([C:23]2[N:27]3[CH:28]=[CH:29][N:30]=[C:31]([CH3:32])[C:26]3=[N:25][C:24]=2[C:33]2[CH:34]=[CH:35][C:36]([F:39])=[CH:37][CH:38]=2)=[N:22][C:17]([NH:16][CH:13]2[CH2:15][CH2:14]2)=[N:18][CH:19]=1

Komponenten

5

Edukt 2

HCID 6909Trichloroisocyanuric AcidHCID 58869555Cyclopropyl-4-[2-(4-fluorophenyl)-8-methylimidazo[1,2-a]pyrazin-3-yl]-pyrimidin-2-ylamine

Produkt 1

HCID 58869564{5-Chloro-4-[2-(4-fluorophenyl)-8-methylimidazo[1,2-a]pyrazin-3-yl]-pyrimidin-2-yl}-cyclopropylamineAusbeute 95 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6212ChloroformLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Trichloroisocyanuric acid (0.001 g, 0.04 mmol) was added portion-wise to a refluxing mixture of cyclopropyl-4-[2-(4-fluorophenyl)-8-methylimidazo[1,2-a]pyrazin-3-yl]-pyrimidin-2-ylamine (Example #A.2.1, 0.050 g, 0.14 mmol) in CHCl3 (2.5 mL). The reaction mixture was refluxed for 3 h, cooled to room temperature, diluted with DCM and washed with a saturated aqueous solution of Na2CO3. The organic phase was dried over MgSO4, filtered, and evaporated. The resulting residue was purified by silica gel chromatography using a gradient of heptane/EtOAc (50:50 to 0:100) to afford 0.015 g (27%) of the title compound. LC/MS (Table 1, Method g) Rt=2.71 min; MS m/z: 393.2 (M+H)+.

Aufarbeitung

  1. temperatureThe reaction mixture was refluxed for 3 h
  2. washwashed with a saturated aqueous solution of Na2CO3
  3. dry with materialThe organic phase was dried over MgSO4
  4. filtrationfiltered
  5. customevaporated
  6. customThe resulting residue was purified by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-ac8d23d1cb1a4aea810109c80e9d4a81
Quelldatensatz
uspto-grants-2010_05
Patentnummer
US07709468B2

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