Dimethylformamide → HCID 68015336, compound

HRID 570686Notes

Reaction equation

HRID 570686 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[C:11](=[O:12])[N:10]([C:13]3[CH:18]=[CH:17][C:16]([O:19][CH2:20][C:21]([F:24])([F:23])[F:22])=[CH:15][CH:14]=3)[C:9](=[S:25])[NH:8][C:7]=2[N:26]=1.C(=O)([O-])O.[Na+].I[CH2:33][CH2:34][CH3:35].CN(C)C=O>O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[C:11](=[O:12])[N:10]([C:13]3[CH:14]=[CH:15][C:16]([O:19][CH2:20][C:21]([F:24])([F:23])[F:22])=[CH:17][CH:18]=3)[C:9]([S:25][CH2:33][CH2:34][CH3:35])=[N:8][C:7]=2[N:26]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 336431-IodopropaneHCID 516892Sodium BicarbonateHCID 866853517-methoxy-2-thioxo-3-[4-(2,2,2-trifluoroethoxy)phenyl]-2,3-dihydropyrido[2,3-d]pyrimidin-4(1H)-one

Product 1

HCID 68015336HCID 68015336, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 7-methoxy-2-thioxo-3-[4-(2,2,2-trifluoroethoxy)phenyl]-2,3-dihydropyrido[2,3-d]pyrimidin-4(1H)-one (153 mg), 1M aqueous sodium hydrogen carbonate solution (439 μl), 1-iodopropane (117 μl) and N,N-dimethylformamide (3 ml) was stirred at 80° C. for 10 min. The reaction mixture was allowed to be cooled, and water (20 ml) was added thereto. The white precipitate was collected by filtration, washed with water, and dissolved in tetrahydrofuran (10 ml). The solution was diluted with ethyl acetate (20 ml), washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the obtained residue was recrystallized from a mixed solvent of ethyl acetate/heptane to give the title compound (114 mg) as cotton-like needle crystals.

Workup

  1. temperatureto be cooled
  2. filtrationThe white precipitate was collected by filtration
  3. washwashed with water
  4. dissolutiondissolved in tetrahydrofuran (10 ml)
  5. additionThe solution was diluted with ethyl acetate (20 ml)
  6. washwashed with water and saturated brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customThe solvent was evaporated under reduced pressure
  9. customthe obtained residue was recrystallized from a mixed solvent of ethyl acetate/heptane

Sources & evidence

ORD record
ord-498140cd55064906b49833ab9d5d0b10
Source dataset
uspto-grants-2015_05
Patent number
US09023858B2

Reaction notes

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