Dimethylformamide → HCID 57429622, compound

HRID 889016Notes

Reaction equation

HRID 889016 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]#[C:9][CH2:10][N:11]2[CH:15]=[C:14]([C:16]3[NH:24][C:23]4[C:22](=[O:25])[N:21]([CH2:26][CH2:27][CH3:28])[C:20](=[O:29])[N:19]([CH2:30][CH2:31][CH3:32])[C:18]=4[N:17]=3)[CH:13]=[N:12]2)=[CH:4][CH:3]=1.[C:33](=O)([O-])[O-].[K+].[K+].CI.CN(C=O)C>O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]#[C:9][CH2:10][N:11]2[CH:15]=[C:14]([C:16]3[N:24]([CH3:33])[C:23]4[C:22](=[O:25])[N:21]([CH2:26][CH2:27][CH3:28])[C:20](=[O:29])[N:19]([CH2:30][CH2:31][CH3:32])[C:18]=4[N:17]=3)[CH:13]=[N:12]2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 44236503HCID 44236503, compound

Product 1

HCID 57429622HCID 57429622, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 8-{1-[3-(4-fluoro-phenyl)-prop-2-ynyl]-1H-pyrazol-4-yl}-1,3-dipropyl-3,7-dihydro-purine-2,6-dione (0.035 g, 0.08 mmol), potassium carbonate (0.022 g, 0.16 mmol), methyl iodide (0.005 ml, 0.088 mmol) and DMF (2 ml) were heated at 50° C. for 20 hour. The mixture was cooled to room temperature and diluted with water (10 ml). The aqueous layer was extracted with ethyl acetate. The organic layer was washed with water and sat. brine solution, and dried over Na2SO4. Solvent was evaporated, the residue obtained was triturated with hexane to obtain the title compound (0.022 g, 61

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. extractionThe aqueous layer was extracted with ethyl acetate
  3. washThe organic layer was washed with water and sat. brine solution
  4. dry with materialdried over Na2SO4
  5. customSolvent was evaporated
  6. customthe residue obtained
  7. customwas triturated with hexane

Sources & evidence

ORD record
ord-11bc07708fe749dbb3c82f655bec3450
Source dataset
uspto-grants-2012_08
Patent number
US08252797B2

Reaction notes

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