Water → HCID 58994149, compound

HRID 12701Notes

Reaction equation

HRID 12701 reaction equation
Cl.[Cl: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]([F: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>[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]([Cl:2])=[N:4][CH:5]=[C:6]([F:17])[CH:7]=2)[C:10](=[O:16])[NH:11][C:12]1=[O:15]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 1189323-Bromopropionaldehyde dimethylacetalHCID 866159455-(2-Chloro-5-fluoro-pyridin-3-yl)-1H-pyrimidine-2,4-dione hydrochloride

Product 1

HCID 58994149HCID 58994149, compoundYield 48.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5-(2-Chloro-5-fluoro-pyridin-3-yl)-1H-pyrimidine-2,4-dione hydrochloride (Prep71, 249 mg, 0.9 mmol), K2CO3 (124 mg, 0.9 mmol) and 3-bromo-1,1dimethoxy-propane (205 mg, 1.1 mmol) were suspended in DMF (3 ml). After stirring the reaction at room temperature for 18 hours, water was added. The aqueous layer washed with diethylether and then the product was extracted with ethyl acetate. The organic phase was dried (Na2SO4) and evaporated to give 150 mg of the final compound that was used without further purification in the next step (48% yield).

Workup

  1. customthe reaction at room temperature for 18 hours
  2. washThe aqueous layer washed with diethylether
  3. extractionthe product was extracted with ethyl acetate
  4. dry with materialThe organic phase was dried (Na2SO4)
  5. customevaporated

Sources & evidence

ORD record
ord-224de5a4eea7482e98c9b75bfc6eabe9
Source dataset
uspto-grants-2010_06
Patent number
US07727988B2

Reaction notes

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