Sodium Methoxide → HCID 178437717, compound

HRID 1458674Notes

Reaction equation

HRID 1458674 reaction equation
Br[C:2]1[C:3]([NH:10][C@H:11]2[CH2:16][CH2:15][C@@H:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:13][CH2:12]2)=[N:4][CH:5]=[N:6][C:7]=1[CH2:8][CH3:9].[CH3:23][O-:24].[Na+]>C(OCC)(=O)C.[Cu]Br>[CH2:8]([C:7]1[N:6]=[CH:5][N:4]=[C:3]([NH:10][C@H:11]2[CH2:16][CH2:15][C@@H:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:13][CH2:12]2)[C:2]=1[O:24][CH3:23])[CH3:9]

Participants

5

Reactant 2

HCID 10942334Sodium MethoxideHCID 178437714HCID 178437714, compound

Product 1

HCID 178437717HCID 178437717, compound

Reagents, catalysts & solvents 2

HCID 24593copper(I) bromideCatalystHCID 8857Ethyl AcetateSolvent2×

Procedure

7.20 g (20 mmol) of 5-bromo-6-ethyl-4-(cis-4-phenylcyclohexylamino)pyrimidine (DE-A-42 08 254) and 0.44 g (3 mmol) of copper(I) bromide were heated under reflux for 12 hours in 10 ml of 30% methanolic sodium methylate solution, to which 0.70 g of ethyl acetate have been added. For working up, the solvent is stripped off, the residue is taken up in ethyl acetate, this mixture is subjected to extraction by stirring with water, and the organic phase is dried and concentrated. For purification, the crude product is chromatographed on silica gel using ethyl acetate/petroleum ether (8:2). 3.7 g (60% of theory) of a colorless oil were obtained which gradually solidified.

Workup

  1. additionhave been added
  2. extractionthis mixture is subjected to extraction
  3. customthe organic phase is dried
  4. concentrationconcentrated
  5. customFor purification
  6. customthe crude product is chromatographed on silica gel
  7. custom3.7 g (60% of theory) of a colorless oil were obtained which

Sources & evidence

ORD record
ord-955e084090b14b6490a917c45e453a75
Source dataset
uspto-grants-1998_12
Patent number
US05852023

Reaction notes

Loading…