Potassium Carbonate → HCID 59496107, compound

HRID 1513329Notes

Reaction equation

HRID 1513329 reaction equation
[CH3:1][C:2]1[C:3](=[O:17])[N:4]([C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:10])[C:5](=[O:8])[NH:6][N:7]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:25][CH2:26][CH:27]([O:30][CH3:31])[O:28][CH3:29]>CN(C)C=O>[CH3:29][O:28][CH:27]([O:30][CH3:31])[CH2:26][CH2:25][N:6]1[C:5](=[O:8])[N:4]([C:9]([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)=[O:10])[C:3](=[O:17])[C:2]([CH3:1])=[N:7]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 1189323-Bromopropionaldehyde dimethylacetalHCID 59496094HCID 59496094, compound

Product 1

HCID 59496107HCID 59496107, compoundYield 70.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 6-methyl-4-(phenylcarbonyl)-1,2,4-triazine-3,5(2H,4H)-dione (P2, 90 mg, 0.389 mmol) in N,N-Dimethylformamide (DMF) (0.6 mL), potassium carbonate (64.6 mg, 0.467 mmol) and 3-bromo-1,1-bis(methyloxy)propane (commercially available from Aldrich, 0.071 mL, 0.467 mmol), were added and the mixture was stirred at rt overnight. The day after the reaction mixture was quenched with water and diluted with AcOEt. Organic phase was washed with water and brine, dried over Na2SO4 and evaporated under reduced pressure. Crude product was purified by flash chromatography (Cy 100% to Cy/AcOEt 6:4) affording the title compound 2-[3,3-bis(methyloxy)propyl]-6-methyl-4-(phenylcarbonyl)-1,2,4-triazine-3,5(2H,4H)-dione (92 mg, 0.276 mmol, 70.9% yield) as a clear oil.

Workup

  1. customThe day after the reaction mixture was quenched with water
  2. additiondiluted with AcOEt
  3. washOrganic phase was washed with water and brine
  4. dry with materialdried over Na2SO4
  5. customevaporated under reduced pressure
  6. customCrude product was purified by flash chromatography (Cy 100% to Cy/AcOEt 6:4)

Sources & evidence

ORD record
ord-b66ad645db6c4db5bbb979ed39420d58
Source dataset
uspto-grants-2012_07
Patent number
US08217168B2

Reaction notes

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