Hydrochloric Acid → HCID 57786346, compound

HRID 1399104Notes

Reaction equation

HRID 1399104 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[Cl:19][C:20]1[CH:21]=[CH:22][C:23]([CH:44]=[O:45])=[C:24]2[C:28]=1[N:27]=[C:26]1[N:29]([C:33]3[C:34]([CH2:42][CH3:43])=[N:35][C:36]([CH3:41])=[N:37][C:38]=3[CH2:39][CH3:40])[CH2:30][CH2:31][CH2:32][N:25]21.C[Si](C)(C)[C:48]([F:51])([F:50])[F:49].Cl.C(=O)([O-])O.[Na+]>O1CCCC1>[Cl:19][C:20]1[C:28]2[N:27]=[C:26]3[N:29]([C:33]4[C:34]([CH2:42][CH3:43])=[N:35][C:36]([CH3:41])=[N:37][C:38]=4[CH2:39][CH3:40])[CH2:30][CH2:31][CH2:32][N:25]3[C:24]=2[C:23]([CH:44]([OH:45])[C:48]([F:51])([F:50])[F:49])=[CH:22][CH:21]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 552549(Trifluoromethyl)trimethylsilaneHCID 2724141Tetrabutylammonium FluorideHCID 57785798HCID 57785798, compound

Product 1

HCID 57786346HCID 57786346, compoundYield 96.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Tetrabutylammonium fluoride (1.0 M solution in tetrahydrofuran, 0.31 mL, 0.31 mmol) was added dropwise to a stirred solution of 9-chloro-1-(4,6-diethyl-2-methylpyrimidin-5-yl)-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazole-6-carbaldehyde (601 mg, 1.57 mmol) and trimethyl(trifluoromethyl)silane (670 mg, 4.71 mmol) in tetrahydrofuran (10 mL) at 0° C., and the mixture was stirred at 0° C. for 90 min. 1N hydrochloric acid (4.0 mL) was added to the mixture at 0° C., and the mixture was stirred at 0° C. for 10 min. The mixture was neutralized 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 70-100% ethyl acetate/n-hexane gradient mixture. The filtrate was concentrated in vacuo to give the title compound as a colorless solid (684 mg, 1.51 mmol, 96%).

Workup

  1. stirringthe mixture was stirred at 0° C. for 10 min
  2. extractionextracted with ethyl acetate
  3. washThe combined organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash column chromatography on silica gel eluting with a 70-100% ethyl acetate/n-hexane gradient mixture
  8. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-4ec957061b924adc934682db517f84d5
Source dataset
uspto-grants-2014_12
Patent number
US08901141B2

Reaction notes

Loading…