Tetrahydrofuran → HCID 57785777, compound

HRID 1628894Notes

Reaction equation

HRID 1628894 reaction equation
[CH:1]1([Mg]Br)[CH2:3][CH2:2]1.[Br:6][C:7]1[CH:8]=[CH:9][C:10]([C:28](OC)=[O:29])=[C:11]2[C:15]=1[N:14]=[C:13]1[N:16]([C:20]3[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][C:21]=3[Cl:27])[CH2:17][CH2:18][CH2:19][N:12]21.O1[CH2:36][CH2:35][CH2:34]C1>>[Br:6][C:7]1[C:15]2[N:14]=[C:13]3[N:16]([C:20]4[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][C:21]=4[Cl:27])[CH2:17][CH2:18][CH2:19][N:12]3[C:11]=2[C:10]([C:28]([CH:34]2[CH2:35][CH2:36]2)([CH:1]2[CH2:3][CH2:2]2)[OH:29])=[CH:9][CH:8]=1

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 57785916HCID 57785916, compoundHCID 178418630HCID 178418630, compound

Product 1

HCID 57785777HCID 57785777, compoundYield 88%

Conditions

Temperature
60 °C

Procedure

Cyclopropylmagnesium bromide (1.0 M solution in tetrahydrofuran, 0.880 mL, 0.880 mmol) was added to a stirred solution of methyl 9-bromo-1-(2,4-dichlorophenyl)-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazole-6-carboxylate (80.0 mg, 0.176 mmol) in tetrahydrofuran (0.88 mL), and the mixture was stirred at 60° C. for 90 min. The reaction was quenched by aqueous saturated ammonium chloride, and the mixture was extracted with ethyl acetate. The combined organic layer was washed with brine, dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel eluting with a 10-40% ethyl acetate/n-hexane gradient mixture to give the title compound as a colorless amorphous solid (78.3 mg, 0.154 mmol, 88%).

Workup

  1. customThe reaction was quenched by aqueous saturated ammonium chloride
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe combined organic layer was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash column chromatography on silica gel eluting with a 10-40% ethyl acetate/n-hexane gradient mixture

Sources & evidence

ORD record
ord-3fe30575c538472ebf43a9793a75ac48
Source dataset
uspto-grants-2014_07
Patent number
US08785460B2

Reaction notes

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