Water → HCID 58994195, compound

HRID 12688Notes

Reaction equation

HRID 12688 reaction equation
Cl.[CH3:2][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].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:6]2[CH:7]=[N:8][C:3]([CH3:2])=[CH:4][CH:5]=2)[C:10](=[O:16])[NH:11][C:12]1=[O:15]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 1189323-Bromopropionaldehyde dimethylacetal2×HCID 686915595-(6-methyl-pyridin-3-yl)-1H-pyrimidine-2,4-dione hydrochloride

Product 1

HCID 58994195HCID 58994195, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5-(6-methyl-pyridin-3-yl)-1H-pyrimidine-2,4-dione hydrochloride (Prep57, 385 mg, 1.62 mmol), K2CO3 (224 mg, 1.62 mmol) and 3-bromo-1,1dimethoxy-propane (commercially available from Aldrich, 183 mg, 1.0 mmol) were suspended in dry DMF (8 mL). After stirring the reaction at room temperature for 24 hours, additional 3-bromo-1,1dimethoxy-propane (180 mg, 0.98 mmol) was added portionwise over a period of 96 h. Water was added and the mixture washed with diethyl ether. The aqueous layer was then extracted with ethyl acetate. The organic phase was dried (Na2SO4) and evaporated to give 320 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 24 hours
  2. washthe mixture washed with diethyl ether
  3. extractionThe aqueous layer was then extracted with ethyl acetate
  4. dry with materialThe organic phase was dried (Na2SO4)
  5. customevaporated

Sources & evidence

ORD record
ord-204e0a98af9b49778d661eaac3535d46
Source dataset
uspto-grants-2010_06
Patent number
US07727988B2

Reaction notes

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