1-[9-Chloro-1-(2-methoxy-4,6-dimethylpyrimidin-5-yl)-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazol-6-yl]-2,2,2-trifluoroethanol → HCID 57786053, compound

HRID 1399366Notes

Reaction equation

HRID 1399366 reaction equation
Cl[C:2]1[C:10]2[N:9]=[C:8]3[N:11]([C:15]4[C:16]([CH3:24])=[N:17][C:18]([O:22][CH3:23])=[N:19][C:20]=4[CH3:21])[CH2:12][CH2:13][CH2:14][N:7]3[C:6]=2[C:5]([CH:25]([OH:30])[C:26]([F:29])([F:28])[F:27])=[CH:4][CH:3]=1>C(O)(=O)C.[Pd]>[F:29][C:26]([F:27])([F:28])[CH:25]([C:5]1[C:6]2[N:7]3[CH2:14][CH2:13][CH2:12][N:11]([C:15]4[C:16]([CH3:24])=[N:17][C:18]([O:22][CH3:23])=[N:19][C:20]=4[CH3:21])[C:8]3=[N:9][C:10]=2[CH:2]=[CH:3][CH:4]=1)[OH:30]

Participants

4

Reactant 1

HCID 577860611-[9-Chloro-1-(2-methoxy-4,6-dimethylpyrimidin-5-yl)-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazol-6-yl]-2,2,2-trifluoroethanol

Product 1

HCID 57786053HCID 57786053, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

To a solution of 1-[9-chloro-1-(2-methoxy-4,6-dimethylpyrimidin-5-yl)-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazol-6-yl]-2,2,2-trifluoroethanol (563 mg, 1.27 mmol) in acetic acid (8.5 mL) was added 10% palladium on carbon (50% wet, 56.3 mg), and the mixture was purged with hydrogen and stirred under balloon pressure hydrogen at room temperature for 2 days. The catalyst was removed by filtration, and the filtrate was concentrated in vacuo. The residue was diluted with saturated aqueous sodium hydrogen carbonate and extracted with ethyl acetate. The combined organic layer was washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo to give a solid, which was recrystallized from methanol to give the title compound as colorless crystals (362 mg, 0.889 mmol, 70%).

Workup

  1. customthe mixture was purged with hydrogen
  2. customThe catalyst was removed by filtration
  3. concentrationthe filtrate was concentrated in vacuo
  4. additionThe residue was diluted with saturated aqueous sodium hydrogen carbonate
  5. extractionextracted with ethyl acetate
  6. washThe combined organic layer was washed with brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customto give a solid, which
  11. customwas recrystallized from methanol

Sources & evidence

ORD record
ord-7562903c66e041bcac5a3f0336d89cff
Source dataset
uspto-grants-2014_12
Patent number
US08901141B2

Reaction notes

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