Potassium Carbonate → HCID 59448369, compound

HRID 1925021Notes

Reaction equation

HRID 1925021 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([C:8]2[C:9](=[O:23])[N:10]([C:15]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[O:16])[C:11](=[O:14])[NH:12][CH:13]=2)[S:5][C:6]=1[CH3:7].C([O-])([O-])=O.[K+].[K+].Br[CH2:31][CH2:32][CH:33]([O:36][CH3:37])[O:34][CH3:35]>CCCC[N+](CCCC)(CCCC)CCCC.[I-].CN(C)C=O.CCOC(C)=O>[CH3:35][O:34][CH:33]([O:36][CH3:37])[CH2:32][CH2:31][N:12]1[CH:13]=[C:8]([C:4]2[S:5][C:6]([CH3:7])=[C:2]([CH3:1])[N:3]=2)[C:9](=[O:23])[N:10]([C:15]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)=[O:16])[C:11]1=[O:14]

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 1189323-Bromopropionaldehyde dimethylacetalHCID 135995202HCID 135995202, compound

Product 1

HCID 59448369HCID 59448369, compoundYield 40.1%

Reagents, catalysts & solvents 3

HCID 67553Tetrabutylammonium IodideCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

5-(4,5-dimethyl-1,3-thiazol-2-yl)-3-(phenylcarbonyl)-2,4(1H,3H)-pyrimidinedione (Prep 16, 80 mg, 0.244 mmol), K2CO3 (33.8 mg, 0.244 mmol), TBAI (9.03 mg, 0.024 mmol) and 3-bromo-1,1-bis(methyloxy)propane (0.033 mL, 0.244 mmol) in dry N,N-Dimethylformamide (DMF) (1.5 mL) were stirred in a closed vial at rt for 2 days then it was left standing at rt over the weekend. The mixture was diluted with EtOAc (20 mL) and washed with small portion of ice-water (3×1 mL). The organic was dried (Na2SO4, rotaevaporator) to afford a crude (95 mg) that was purified by silica chromatography, eluting with Cyclohexane:EtOAc 100:0 to 50:50 to afford the title compound as a white solid (42 mg).

Workup

  1. waitit was left
  2. customstanding at rt over the weekend
  3. washwashed with small portion of ice-water (3×1 mL)
  4. dry with materialThe organic was dried (Na2SO4, rotaevaporator)
  5. customto afford a crude (95 mg) that
  6. customwas purified by silica chromatography
  7. washeluting with Cyclohexane:EtOAc 100:0 to 50:50

Sources & evidence

ORD record
ord-72e79112eaab4b57a99b7ae559de8b92
Source dataset
uspto-grants-2012_05
Patent number
US08178549B2

Reaction notes

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