Tetrahydrofuran → HCID 57786019, compound

HRID 1399102Notes

Reaction equation

HRID 1399102 reaction equation
[CH:1]1([Mg]Br)[CH2:3][CH2:2]1.[Cl:6][C:7]1[CH:8]=[CH:9][C:10]([C:28]([O:30]C)=O)=[C:11]2[C:15]=1[N:14]=[C:13]1[N:16]([C:20]3[C:25]([CH3:26])=[N:24][C:23]([CH3:27])=[CH:22][N:21]=3)[CH2:17][CH2:18][CH2:19][N:12]21.O1[CH2:36][CH2:35][CH2:34]C1>>[Cl:6][C:7]1[C:15]2[N:14]=[C:13]3[N:16]([C:20]4[C:25]([CH3:26])=[N:24][C:23]([CH3:27])=[CH:22][N:21]=4)[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:30])=[CH:9][CH:8]=1

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 57786191HCID 57786191, compoundHCID 178418630HCID 178418630, compound

Product 1

HCID 57786019HCID 57786019, compoundYield 35%

Conditions

Temperature
60 °C

Procedure

Cyclopropylmagnesium bromide (1.0 M solution in tetrahydrofuran, 1.59 mL, 1.59 mmol) was added to a stirred solution of methyl 9-chloro-1-(3,5-dimethylpyrazin-2-yl)-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazole-6-carboxylate (148 mg, 0.398 mmol) in tetrahydrofuran (2.0 mL), and the mixture was stirred at 60° C. for 3 hr. 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 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 solid, which was recrystallized from ethyl acetate to give the title compound as a colorless crystal (59.7 mg, 0.141 mmol, 35%).

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 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
  9. customto give the solid, which
  10. customwas recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-dd05c4536ef5410f96043269bd471b7f
Source dataset
uspto-grants-2014_12
Patent number
US08901141B2

Reaction notes

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