Water → HCID 58994220, compound

HRID 12724Notes

Reaction equation

HRID 12724 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][C:6]([CH3:17])=[CH:5][N:4]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:25][CH2:26][CH:27]([O:30][CH3:31])[O:28][CH3:29].O>CN(C=O)C>[F:2][C:3]1[C:8]([C:9]2[C:10](=[O:16])[NH:11][C:12](=[O:15])[N:13]([CH2:25][CH2:26][CH:27]([O:30][CH3:31])[O:28][CH3:29])[CH:14]=2)=[CH:7][C:6]([CH3:17])=[CH:5][N:4]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 1189323-Bromopropionaldehyde dimethylacetalHCID 686920285-(2-Fluoro-5-methyl-pyridin-3-yl)-1H-pyrimidine-2,4-dione hydrochloride

Product 1

HCID 58994220HCID 58994220, compoundYield 53.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 5-(2-fluoro-5-methyl-pyridin-3-yl)-1H-pyrimidine-2,4-dione hydrochloride (Prep99, 300 mg, 1.16 mmol), and K2CO3 (241 mg, 1.7 mmol) in DMF (5 ml) was stirred for one hour at room temperature. 3-Bromo-1,1dimethoxy-propane (234 mg, 1.3 mmol) was added and stirring was continued for three days. Water was added and the product was extracted with ethyl acetate. The organic phase was dried (Na2SO4), filtered and evaporated. The crude was purified by flash chromatography eluting with DCM-MeOH—NH4OH (95:5:0.5) to give 200 mg of the final compound as oil (53% yield).

Workup

  1. stirringstirring
  2. waitwas continued for three days
  3. extractionthe product was extracted with ethyl acetate
  4. dry with materialThe organic phase was dried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated
  7. customThe crude was purified by flash chromatography
  8. washeluting with DCM-MeOH—NH4OH (95:5:0.5)

Sources & evidence

ORD record
ord-393ef3ff47e94b2ea6bc61546aef45a0
Source dataset
uspto-grants-2010_06
Patent number
US07727988B2

Reaction notes

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