Water → HCID 58994226, compound

HRID 12745Notes

Reaction equation

HRID 12745 reaction equation
Cl.[N:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[C:8]1[C:9](=[O:15])[NH:10][C:11](=[O:14])[NH:12][CH:13]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:23][CH2:24][CH:25]([O:28][CH3:29])[O:26][CH3:27].O>CN(C=O)C>[CH3:27][O:26][CH:25]([O:28][CH3:29])[CH2:24][CH2:23][N:12]1[CH:13]=[C:8]([C:3]2[CH:4]=[N:5][CH:6]=[CH:7][N:2]=2)[C:9](=[O:15])[NH:10][C:11]1=[O:14]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 1189323-Bromopropionaldehyde dimethylacetalHCID 686969295-Pyrazin-2-yl-1H-pyrimidine-2,4-dione hydrochloride

Product 1

HCID 58994226HCID 58994226, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 5-pyrazin-2-yl-1H-pyrimidine-2,4-dione hydrochloride (Prep125, 2.19 mmol), and K2CO3 (302 mg, 2.19 mmol) in DMF (20 ml) was stirred 30 minutes at room temperature. 90% 3-Bromo-1,1dimethoxy-propane (365 μl, 2.41 mmol) was added in two portions during 2 days. Water was added and the mixture 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 (98-2-0.2) to give 221 mg of the title compound (35% yield).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialThe organic phase was dried (Na2SO4)
  3. filtrationfiltered
  4. customevaporated
  5. customThe crude was purified by flash chromatography
  6. washeluting with DCM-MeOH—NH4OH (98-2-0.2)

Sources & evidence

ORD record
ord-8a7008fcf016486bb7b985cf8340c0ce
Source dataset
uspto-grants-2010_06
Patent number
US07727988B2

Reaction notes

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