2-Amino-4,6-dichloropyrimidine → HCID 178508440, compound

HRID 2367406Notes

Reaction equation

HRID 2367406 reaction equation
[Cl: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]([Cl: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 178477902HCID 178477902, compound

Product 1

HCID 178508440HCID 178508440, compoundYield 97.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
85 °C

Procedure

To a solution of 5-chloro-2-(2-morpholinyl)-1H-benzimidazole (200 mg, 0.841 mmol) and Hunig's base (109 mg, 0.841 mmol) in ethanol (10 mL) stirred at room temperature was added 4,6-dichloro-2-pyrimidinamine (138 mg, 0.841 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 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 (300 mg). LC-MS (ES) m/z=365, 367 [M+H]+.

Workup

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

Sources & evidence

ORD record
ord-ed67b46a00ed4ca59a6923926f7cb46e
Source dataset
uspto-grants-2014_04
Patent number
US08697685B2

Reaction notes

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