2-Amino-4,6-dichloropyrimidine → HCID 178508441, compound

HRID 2367411Notes

Reaction equation

HRID 2367411 reaction equation
[F:1][C:2]1[CH:16]=[CH:15][C:5]2[NH:6][C:7]([CH:9]3[O:14][CH2:13][CH2:12][NH:11][CH2:10]3)=[N:8][C:4]=2[CH:3]=1.CCN(C(C)C)C(C)C.[Cl:26][C:27]1[CH:32]=[C:31](Cl)[N:30]=[C:29]([NH2:34])[N:28]=1>C(O)C>[Cl:26][C:27]1[CH:32]=[C:31]([N:11]2[CH2:12][CH2:13][O:14][CH:9]([C:7]3[NH:6][C:5]4[CH:15]=[CH:16][C:2]([F:1])=[CH:3][C:4]=4[N:8]=3)[CH2:10]2)[N:30]=[C:29]([NH2:34])[N:28]=1

Participants

5

Reactant 3

HCID 655222-Amino-4,6-dichloropyrimidineHCID 81531DiisopropylethylamineHCID 178505466HCID 178505466, compound

Product 1

HCID 178508441HCID 178508441, compoundYield 79.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of 5-fluoro-2-(2-morpholinyl)-1H-benzimidazole (200 mg, 0.904 mmol) and Hunig's base (409 mg, 3.16 mmol) in ethanol (10 mL) stirred at room temperature was added 4,6-dichloro-2-pyrimidinamine (148 mg, 0.904 mmol), and the reaction mixture was stirred overnight at 85° C. The reaction mixture was cooled to room temperature and partitioned between EtOAc (25 mL) and water (25 mL). The organic solvent was evaporated in vacuo to give the crude product. The residue was triturated with EtOAc (1×5 mL). The resulting solid was filtered and collected to afford the title compound (250 mg). LC-MS (ES) m/z=349 [M+H]+.

Workup

  1. stirringthe reaction mixture was stirred overnight at 85° C
  2. temperatureThe reaction mixture was cooled to room temperature
  3. custompartitioned between EtOAc (25 mL) and water (25 mL)
  4. customThe organic solvent was evaporated in vacuo
  5. customto give the crude product
  6. customThe residue was triturated with EtOAc (1×5 mL)
  7. filtrationThe resulting solid was filtered
  8. customcollected

Sources & evidence

ORD record
ord-0212f032aebc4079afeb08ff84aba3ce
Source dataset
uspto-grants-2014_04
Patent number
US08697685B2

Reaction notes

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