Water → HCID 58994249, compound

HRID 12734Notes

Reaction equation

HRID 12734 reaction equation
Cl.[CH3:2][C:3]1[CH:8]=[CH:7][N:6]=[CH:5][C:4]=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].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:4]2[CH:5]=[N:6][CH:7]=[CH:8][C:3]=2[CH3:2])[C:10](=[O:16])[NH:11][C:12]1=[O:15]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 1189323-Bromopropionaldehyde dimethylacetalHCID 686934255-(4-methyl-pyridin-3-yl)-1H-pyrimidine-2,4-dione hydrochloride

Product 1

HCID 58994249HCID 58994249, compoundYield 27%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 5-(4-methyl-pyridin-3-yl)-1H-pyrimidine-2,4-dione hydrochloride (Prep 11, 605 mg, 2.53 mmol) and K2CO3 (349 mg, 2.53 mmol) in DMF (10 ml), 3-bromo-1,1dimethoxy-propane (399 μl, 2.78 mmol) was added in two portions over 2 days and the mixture was contemporarily stirred at room temperature. Water was then added and washed with Et2O, 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 (98-2-02) to give 100 mg of the title compound (27% yield).

Workup

  1. additionwas added in two portions over 2 days
  2. washwashed with Et2O
  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 (98-2-02)

Sources & evidence

ORD record
ord-043bcf02c51242e2bb6799e4f06c9ef6
Source dataset
uspto-grants-2010_06
Patent number
US07727988B2

Reaction notes

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