Hydrochloric Acid → 1-[3,3-bis(methyloxy)propyl]-5-(2-methyl-1,3-thiazol-4-yl)-2,4(1H,3H)-pyrimidinedione

HRID 1925024Notes

Reaction equation

HRID 1925024 reaction equation
Cl.[CH3:2][C:3]1[S:4][CH:5]=[C:6]([C:8]2[C:9](=[O:15])[NH:10][C:11](=[O:14])[NH:12][CH:13]=2)[N:7]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:23][CH2:24][CH:25]([O:28][CH3:29])[O:26][CH3:27].Cl>CN(C)C=O.O>[CH3:27][O:26][CH:25]([O:28][CH3:29])[CH2:24][CH2:23][N:12]1[CH:13]=[C:8]([C:6]2[N:7]=[C:3]([CH3:2])[S:4][CH:5]=2)[C:9](=[O:15])[NH:10][C:11]1=[O:14]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 1189323-Bromopropionaldehyde dimethylacetalHCID 675196935-(2-methyl-1,3-thiazol-4-yl)-2,4(1H,3H)-pyrimidinedione hydrochloride

Product 1

HCID 594483461-[3,3-bis(methyloxy)propyl]-5-(2-methyl-1,3-thiazol-4-yl)-2,4(1H,3H)-pyrimidinedioneYield 16.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

5-(2-methyl-1,3-thiazol-4-yl)-2,4(1H,3H)-pyrimidinedione hydrochloride (Prep20, 287 mg, 1.110 mmol) was dissolved in N,N-Dimethylformamide (DMF) (4 ml). K2CO3(460 mg, 3.33 mmol) were added and the reaction mixture stirred at room temperature for 1 h. 3-bromo-1,1-bis(methyloxy)propane (0.185 ml, 1.221 mmol) was added. The obtained mixture was then stirred at room temperature. After 4 days it was diluted with water, neutralized with HCl, and extracted by EtOAc. The organic phase was washed with water (3 times), brine, dried over Na2SO4, filtered and the solvent evaporated. The obtained crude was purified by preparative LC-MS. 58.5 mg of the title compound were isolated as a white solid.

Workup

  1. stirringThe obtained mixture was then stirred at room temperature
  2. extractionextracted by EtOAc
  3. washThe organic phase was washed with water (3 times), brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customthe solvent evaporated
  7. customThe obtained crude
  8. customwas purified by preparative LC-MS

Sources & evidence

ORD record
ord-c9aa1040da954c10aa125963e6c702bb
Source dataset
uspto-grants-2012_05
Patent number
US08178549B2

Reaction notes

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