Tetrahydrofuran → HCID 44156497, compound

HRID 1399248Notes

Reaction equation

HRID 1399248 reaction equation
[CH:1]1([Mg]Br)[CH2:3][CH2:2]1.[Cl:6][C:7]1[CH:12]=[C:11]([Cl:13])[CH:10]=[CH:9][C:8]=1[N:14]1[C:19]2=[N:20][C:21]3[C:22](=[C:23]([C:29](OC)=[O:30])[CH:24]=[CH:25][C:26]=3[O:27][CH3:28])[N:18]2[CH2:17][CH2:16][CH2:15]1.O1[CH2:37][CH2:36][CH2:35]C1>>[CH:1]1([C:29]([CH:35]2[CH2:36][CH2:37]2)([C:23]2[C:22]3[N:18]4[CH2:17][CH2:16][CH2:15][N:14]([C:8]5[CH:9]=[CH:10][C:11]([Cl:13])=[CH:12][C:7]=5[Cl:6])[C:19]4=[N:20][C:21]=3[C:26]([O:27][CH3:28])=[CH:25][CH:24]=2)[OH:30])[CH2:3][CH2:2]1

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 57786239HCID 57786239, compoundHCID 178418630HCID 178418630, compound

Product 1

HCID 44156497HCID 44156497, compoundYield 80%

Conditions

Temperature
60 °C

Procedure

Cyclopropylmagnesium bromide (1.0 M solution in tetrahydrofuran, 0.640 mL, 0.640 mmol) was added to a stirred suspension of methyl 1-(2,4-dichlorophenyl)-9-methoxy-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazole-6-carboxylate (52.0 mg, 0.128 mmol) in tetrahydrofuran (0.64 mL), and the mixture was stirred at 60° C. for 30 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 solid (47.4 mg, 0.103 mmol, 80%).

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-af954ed8b5fa4d1b8c775a9176271df0
Source dataset
uspto-grants-2014_12
Patent number
US08901141B2

Reaction notes

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