Ethyl Acetate → HCID 58994156, compound

HRID 12697Notes

Reaction equation

HRID 12697 reaction equation
Cl.[F:2][C:3]1[CH:4]=[N:5][CH:6]=[CH:7][C:8]=1[C:9]1[C:10](=[O:16])[NH:11][C:12](=[O:15])[NH:13][CH:14]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:24][CH2:25][CH:26]([O:29][CH3:30])[O:27][CH3:28].C(OCC)(=O)C>CN(C=O)C>[CH3:28][O:27][CH:26]([O:29][CH3:30])[CH2:25][CH2:24][N:13]1[CH:14]=[C:9]([C:8]2[CH:7]=[CH:6][N:5]=[CH:4][C:3]=2[F:2])[C:10](=[O:16])[NH:11][C:12]1=[O:15]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 1189323-Bromopropionaldehyde dimethylacetalHCID 686942765-(3-Fluoro-pyridin-4-yl)-1H-pyrimidine-2,4-dione hydrochloride

Product 1

HCID 58994156HCID 58994156, compoundYield 22%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5-(3-Fluoro-pyridin-4-yl)-1H-pyrimidine-2,4-dione hydrochloride (Prep 67, 243 mg, 1.1 mmol) was dissolved in DMF (2 ml). K2CO3 (153 mg, 1.1 mmol) was added and the mixture was stirred at room temperature for 1 hour. 3-Bromo-1,1dimethoxy-propane (225 mg, 1.11 mmol) was then added and after stirring the reaction at room temperature for 48 hours, the reaction was left at 4° C. for 17 days. Ethyl acetate was then added and the mixture washed with water and brine. The organic phase was dried (Na2SO4) and evaporated. The residue was purified by flash chromatography with DCM-MeOH—NH4OH 98-2-0.2 to afford 75 mg of the title compound (22% yield).

Workup

  1. stirringafter stirring
  2. customthe reaction at room temperature for 48 hours
  3. waitthe reaction was left at 4° C. for 17 days
  4. washthe mixture washed with water and brine
  5. dry with materialThe organic phase was dried (Na2SO4)
  6. customevaporated
  7. customThe residue was purified by flash chromatography with DCM-MeOH—NH4OH 98-2-0.2

Sources & evidence

ORD record
ord-139880581b8140598e60dce3f19e2b8f
Source dataset
uspto-grants-2010_06
Patent number
US07727988B2

Reaction notes

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