Potassium Carbonate → HCID 58994245, compound

HRID 12738Notes

Reaction equation

HRID 12738 reaction equation
Cl.[F:2][C:3]1[C:8]([C:9]2[C:10](=[O:16])[NH:11][C:12](=[O:15])[NH:13][CH:14]=2)=[CH:7][CH:6]=[C:5]([CH3:17])[N:4]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:25][CH2:26][CH:27]([O:30][CH3:31])[O:28][CH3:29]>CN(C=O)C>[CH3:29][O:28][CH:27]([O:30][CH3:31])[CH2:26][CH2:25][N:13]1[CH:14]=[C:9]([C:8]2[C:3]([F:2])=[N:4][C:5]([CH3:17])=[CH:6][CH:7]=2)[C:10](=[O:16])[NH:11][C:12]1=[O:15]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 1189323-Bromopropionaldehyde dimethylacetalHCID 686914385-(2-Fluoro-6-methyl-pyridin-3-yl)-1H-pyrimidine-2,4-dione hydrochloride

Product 1

HCID 58994245HCID 58994245, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 5-(2-fluoro-6-methyl-pyridin-3-yl)-1H-pyrimidine-2,4-dione hydrochloride (Prep 15, 667 mg, 2.59 mmol), and K2CO3 (358 mg, 2.59 mmol) in DMF (25 ml) was stirred 30 minutes at room temperature. Then 90% 3-Bromo-1,1dimethoxy-propane (432 μl, 2.85 mmol) was added in three portions during 3 days. Solvent was then removed under vacuum at 40° C. and the residue washed with ethyl acetate. The organic phase was dried (Na2SO4), filtered and evaporated. The crude was purified by flash chromatography eluting with DCM-MeOH—NH4OH (98-2-0.2) to give 291 mg of the title compound as a white solid (35% yield).

Workup

  1. customSolvent was then removed under vacuum at 40° C.
  2. washthe residue washed with ethyl acetate
  3. dry with materialThe organic phase was dried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated
  6. customThe crude was purified by flash chromatography
  7. washeluting with DCM-MeOH—NH4OH (98-2-0.2)

Sources & evidence

ORD record
ord-d458da18ea134918a5043b29ba1bb36d
Source dataset
uspto-grants-2010_06
Patent number
US07727988B2

Reaction notes

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