Potassium Carbonate → 1-[3,3-bis(methyloxy)propyl]-5-(2,4-dimethyl-1,3-thiazol-5-yl)-2,4(1H,3H)-pyrimidinedione

HRID 1925036Notes

Reaction equation

HRID 1925036 reaction equation
[CH3:1][C:2]1[S:3][C:4]([C:8]2[C:9](=[O:15])[NH:10][C:11](=[O:14])[NH:12][CH:13]=2)=[C:5]([CH3:7])[N:6]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:23][CH2:24][CH:25]([O:28][CH3:29])[O:26][CH3:27]>CN(C)C=O>[CH3:27][O:26][CH:25]([O:28][CH3:29])[CH2:24][CH2:23][N:12]1[CH:13]=[C:8]([C:4]2[S:3][C:2]([CH3:1])=[N:6][C:5]=2[CH3:7])[C:9](=[O:15])[NH:10][C:11]1=[O:14]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 1189323-Bromopropionaldehyde dimethylacetalHCID 594483615-(2,4-dimethyl-1,3-thiazol-5-yl)-2,4(1H,3H)-pyrimidinedione

Product 1

HCID 594483571-[3,3-bis(methyloxy)propyl]-5-(2,4-dimethyl-1,3-thiazol-5-yl)-2,4(1H,3H)-pyrimidinedioneYield 38.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of 5-(2,4-dimethyl-1,3-thiazol-5-yl)-2,4(1H,3H)-pyrimidinedione (Prep34, 250 mg, 1.120 mmol) in N,N-Dimethylformamide (DMF) (4 mL), Potassium carbonate (124 mg, 0.896 mmol) was added and the mixture was stirred at rt for 1 hour. Afterwards 3-bromo-1,1-bis(methyloxy)propane (0.170 mL, 1.120 mmol) was added dropwise and the reaction mixture was stirred at rt overnight. The day after the reaction was quenched with water and extracted with AcOEt. Organic phase was dried over Na2SO4 and concentrated under vacuum providing a crude as a clear oil. The latter was purified by flash chromatography (eluent:DCM/MeOH/NH3 97:3:0.1) affording the title compound (155 mg, 0.429 mmol) as a white solid.

Workup

  1. additionwas added
  2. stirringthe reaction mixture was stirred at rt overnight
  3. customThe day after the reaction was quenched with water
  4. extractionextracted with AcOEt
  5. dry with materialOrganic phase was dried over Na2SO4
  6. concentrationconcentrated under vacuum
  7. customproviding a crude as a clear oil
  8. customThe latter was purified by flash chromatography (eluent:DCM/MeOH/NH3 97:3:0.1)

Sources & evidence

ORD record
ord-8a3f806c88c54cb9b5ca9adc3fa41574
Source dataset
uspto-grants-2012_05
Patent number
US08178549B2

Reaction notes

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