Water → HCID 67520970, compound

HRID 1925965Notes

Reaction equation

HRID 1925965 reaction equation
[C:1]([O:9][CH2:10]/[CH:11]=[CH:12]/[C:13]1[NH:21][C:20]2[C:19]([O:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[N:18][CH:17]=[N:16][C:15]=2[CH:14]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:29](=O)([O-])[O-].[K+].[K+].IC.O>CN(C)C=O>[C:1]([O:9][CH2:10]/[CH:11]=[CH:12]/[C:13]1[N:21]([CH3:29])[C:20]2[C:19]([O:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[N:18][CH:17]=[N:16][C:15]=2[CH:14]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 67520551HCID 67520551, compound

Product 1

HCID 67520970HCID 67520970, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(2E)-3-(4-Phenoxy-5H-pyrrolo[3,2-d]pyrimidin-6-yl)-2-propenyl benzoate (500 mg) was dissolved in N,N-dimethylformamide (4 mL), and potassium carbonate (279 mg) and iodomethane (0.1 mL) were sequentially added. After stirring at room temperature for 4 hrs, water (30 mL) was added to the reaction mixture and the mixture was extracted with ethyl acetate (100 mL), dried over magnesium sulfate and concentrated under reduced pressure. The residue was separated and purified by basic silica gel column chromatography (eluent, hexane:ethyl acetate=80:20→50:50) to give the title compound (301 mg) as crystals.

Workup

  1. extractionthe mixture was extracted with ethyl acetate (100 mL)
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was separated
  5. custompurified by basic silica gel column chromatography (eluent, hexane:ethyl acetate=80:20→50:50)

Sources & evidence

ORD record
ord-fd9585375f164d09b324bb2f3ae2449e
Source dataset
uspto-grants-2012_05
Patent number
US08178543B2

Reaction notes

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