Methyl Ethyl Ketone → 1-(2,4-Dichlorophenyl)-N-(1-methylpropyl)-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazol-6-amine

HRID 1399122

Reaction equation

HRID 1399122 reaction equation
C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[Cl:15][C:16]1[CH:21]=[C:20]([Cl:22])[CH:19]=[CH:18][C:17]=1[N:23]1[C:28]2=[N:29][C:30]3[C:31](=[C:32]([NH2:36])[CH:33]=[CH:34][CH:35]=3)[N:27]2[CH2:26][CH2:25][CH2:24]1.[CH3:37][C:38](=O)[CH2:39][CH3:40]>CO.C(=O)([O-])O.[Na+]>[Cl:15][C:16]1[CH:21]=[C:20]([Cl:22])[CH:19]=[CH:18][C:17]=1[N:23]1[C:28]2=[N:29][C:30]3[C:31](=[C:32]([NH:36][CH:38]([CH3:37])[CH2:39][CH3:40])[CH:33]=[CH:34][CH:35]=3)[N:27]2[CH2:26][CH2:25][CH2:24]1

Participants

6

Reactant 3

HCID 6569Methyl Ethyl KetoneHCID 5049666Sodium triacetoxyborohydrideHCID 577861701-(2,4-Dichlorophenyl)-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazol-6-amine

Product 1

HCID 577859871-(2,4-Dichlorophenyl)-N-(1-methylpropyl)-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazol-6-amineYield 40%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 516892Sodium BicarbonateSolvent

Procedure

Sodium triacetoxyborohydride (171 mg, 0.807 mmol) was added to a stirred solution of 1-(2,4-dichlorophenyl)-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazol-6-amine (183 mg, 0.549 mmol) and butan-2-one (1.0 mL) in methanol (1.0 ml) at 0° C., and the mixture was stirred at room temperature for 8 hr. The mixture 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. The residue was purified by flash column chromatography on silica gel eluting with a 5-50% ethyl acetate/n-hexane gradient mixture. The filtrate was concentrated in vacuo to give the solid, which was recrystallized from ethyl acetate/n-hexane to give the title compound as a colorless crystal (86.4 mg, 0.222 mmol, 40%).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe combined organic layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash column chromatography on silica gel eluting with a 5-50% ethyl acetate/n-hexane gradient mixture
  7. concentrationThe filtrate was concentrated in vacuo
  8. customto give the solid, which
  9. customwas recrystallized from ethyl acetate/n-hexane

Sources & evidence

ORD record
ord-d5f5c40d49f945038d54c469baba06c5
Source dataset
uspto-grants-2014_12
Patent number
US08901141B2

Linked notes

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