Water → HCID 58994201, compound

HRID 12705Notes

Reaction equation

HRID 12705 reaction equation
Cl.[F:2][C:3]1[N:8]=[C:7]([C:9]2[C:10](=[O:16])[NH:11][C:12](=[O:15])[NH:13][CH:14]=2)[CH:6]=[CH:5][CH:4]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:24][CH2:25][CH:26]([O:29][CH3:30])[O:27][CH3:28].O>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:7]2[CH:6]=[CH:5][CH:4]=[C:3]([F:2])[N:8]=2)[C:10](=[O:16])[NH:11][C:12]1=[O:15]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 1189323-Bromopropionaldehyde dimethylacetalHCID 686903145-(6-Fluoro-pyridin-2-yl)-1H-pyrimidine-2,4-dione hydrochloride

Product 1

HCID 58994201HCID 58994201, compoundYield 70.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 5-(6-Fluoro-pyridin-2-yl)-1H-pyrimidine-2,4-dione hydrochloride (Prep75, 200 mg, 0.82 mmol), and K2CO3 (169 mg, 1.23 mmol) in DMF (4 ml) was stirred 1 hour at room temperature. 3-Bromo-1,1dimethoxy-propane (165 mg, 0.90 mmol) was added and stirring was continued for 48 hours. Water (50 ml) was added and the product was extracted with ethyl acetate. The organic phase was dried (Na2SO4) and evaporated. The crude was triturated with iPr2O to give 179 mg of the final compound as a white solid (70% yield).

Workup

  1. stirringstirring
  2. waitwas continued for 48 hours
  3. extractionthe product was extracted with ethyl acetate
  4. dry with materialThe organic phase was dried (Na2SO4)
  5. customevaporated
  6. customThe crude was triturated with iPr2O

Sources & evidence

ORD record
ord-e9f8b59231f648d7990315cef63ab5fc
Source dataset
uspto-grants-2010_06
Patent number
US07727988B2

Reaction notes

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