Potassium Carbonate → HCID 58994161, compound

HRID 12741Notes

Reaction equation

HRID 12741 reaction equation
Cl.[N:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]2[C:9](=[O:15])[NH:10][C:11](=[O:14])[NH:12][CH:13]=2)[N:3]=1.Br[CH2:17][CH2:18][CH:19]([O:22][CH3:23])[O:20][CH3:21].C([O-])([O-])=O.[K+].[K+]>CS(C)=O>[CH3:21][O:20][CH:19]([O:22][CH3:23])[CH2:18][CH2:17][N:12]1[CH:13]=[C:8]([C:4]2[N:3]=[N:2][CH:7]=[CH:6][CH:5]=2)[C:9](=[O:15])[NH:10][C:11]1=[O:14]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 1189323-Bromopropionaldehyde dimethylacetal3×HCID 68691580HCID 68691580, compound

Product 1

HCID 58994161HCID 58994161, compoundYield 24%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of 5-pyridazin-3-yl-1H-pyrimidine-2,4-dione hydrochloride (Prep121, 656 mg, 2.89 mmol), 3-bromo-1,1dimethoxy-propane (609 mg, 3.33 mmol) and K2CO3 (400 mg, 2.89 mmol) in DMSO (10 ml) was stirred for 24 hours at room temperature. 3-Bromo-1, 1dimethoxy-propane (100 mg, 0.55 mmol) was then added and the reaction was left for 11 days at room temperature. 3-Bromo-1,1dimethoxy-propane (100 mg, 0.55 mmol) was further added and stirring continued for additional 6 days. The mixture was lyophilized and the residue washed with diethyl ether and filtrate. The solid washed with ethyl acetate. After evaporation of the organic phase, 200 mg of the title compound as a light brown powder was obtained (24% yield).

Workup

  1. waitthe reaction was left for 11 days at room temperature
  2. stirringstirring
  3. waitcontinued for additional 6 days
  4. washthe residue washed with diethyl ether and filtrate
  5. washThe solid washed with ethyl acetate
  6. customAfter evaporation of the organic phase

Sources & evidence

ORD record
ord-71c0abedd2864bd4bb2cd0656b11195b
Source dataset
uspto-grants-2010_06
Patent number
US07727988B2

Reaction notes

Loading…