1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 21075459, compound

HRID 1373717Notes

Reaction equation

HRID 1373717 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9](=O)[C:10]([OH:12])=[O:11].C1CCN2C(=NCCC2)CC1.[NH2:25][C:26]1[C:31]([CH:32]=O)=[CH:30][N:29]=[C:28]([S:34][CH3:35])[N:27]=1>CN(C=O)C>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:9]([C:10]([OH:12])=[O:11])=[N:25][C:26]2[N:27]=[C:28]([S:34][CH3:35])[N:29]=[CH:30][C:31]=2[CH:32]=1

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 2957694-Amino-2-(methylsulfanyl)pyrimidine-5-carbaldehydeHCID 14171747Benzenepropanoic acid, 2-broMo-.alpha.-oxo-

Product 1

HCID 21075459HCID 21075459, compoundYield 53.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3.372 g 3-(2-bromophenyl)2-oxopropionic acid in 20 ml DMF were treated with 4.434 g DBU under cooling and stirred for 10 min at RT. 2.728 g 4-amino-2-methylsulfanylpyrimidine-5-carbaldehyde were added and the mixture was stirred at 85° C. for 4.5 hrs. Stirring was continued over night at RT, then the solvent was evaporated and the residue dispensed in aqueous sodium carbonate solution. The mixture is extracted with ethyl acetate, then acidified to pH 2 and again extracted with chloroform. The chloroform extracts were dried and evaporated and the residue triturated with hot ethyl acetate. 2.786 g of the title product were thus obtained after filtration.

Workup

  1. temperatureunder cooling
  2. stirringthe mixture was stirred at 85° C. for 4.5 hrs
  3. stirringStirring
  4. waitwas continued over night at RT
  5. customthe solvent was evaporated
  6. extractionThe mixture is extracted with ethyl acetate
  7. extractionagain extracted with chloroform
  8. dry with materialThe chloroform extracts were dried
  9. customevaporated
  10. customthe residue triturated with hot ethyl acetate

Sources & evidence

ORD record
ord-7c0c22b7683747ef9b1ce3ecfe7609f3
Source dataset
uspto-grants-2007_01
Patent number
US07163941B2

Reaction notes

Loading…