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

HRID 2233116Notes

Reaction equation

HRID 2233116 reaction equation
[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

Participants

5

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

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)+.

Workup

  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

Sources & evidence

ORD record
ord-ac8d23d1cb1a4aea810109c80e9d4a81
Source dataset
uspto-grants-2010_05
Patent number
US07709468B2

Reaction notes

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