Potassium Carbonate → 5-(6-Chloro-pyridin-3-yl)-1-(3,3-dimethoxy-propyl)-1H-pyrimidine-2,4-dione

HRID 12716Notes

Reaction equation

HRID 12716 reaction equation
Cl.[Cl:2][C:3]1[N:8]=[CH:7][C:6]([C:9]2[C:10](=[O:16])[NH:11][C:12](=[O:15])[NH:13][CH:14]=2)=[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]>CN(C=O)C>[Cl:2][C:3]1[N:8]=[CH:7][C:6]([C:9]2[C:10](=[O:16])[NH:11][C:12](=[O:15])[N:13]([CH2:24][CH2:25][CH:26]([O:29][CH3:30])[O:27][CH3:28])[CH:14]=2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 1189323-Bromopropionaldehyde dimethylacetalHCID 866159485-(6-Chloro-pyridin-3-yl)-1H-pyrimidine-2,4-dione hydrochloride

Product 1

HCID 589941995-(6-Chloro-pyridin-3-yl)-1-(3,3-dimethoxy-propyl)-1H-pyrimidine-2,4-dioneYield 40%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 5-(6-chloro-pyridin-3-yl)-1H-pyrimidine-2,4-dione hydrochloride (Prep91, 1.05 g, 4.10 mmol), and K2CO3 (565 mg, 4.10 mmol) in DMF (20 ml) was stirred 20 minutes at room temperature. 3-Bromo-1,1dimethoxy-propane (635 μl, 4.65 mmol) was added in three portions over 6 days. Solvent was then removed under vacuum at 40° C. and the residue washed once with petroleum ether and twice with ethyl acetate. Ethyl acetate 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 534 mg of the title compound as a white solid (40% yield).

Workup

  1. customSolvent was then removed under vacuum at 40° C.
  2. washthe residue washed once with petroleum ether and twice with ethyl acetate
  3. dry with materialEthyl acetate 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-cbb08e8ad456443e8d4d55ae46eccee5
Source dataset
uspto-grants-2010_06
Patent number
US07727988B2

Reaction notes

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