Ethanol → HCID 54011110, compound

HRID 355299Notes

Reaction equation

HRID 355299 reaction equation
Cl[C:2]1[C:7]([CH2:8][CH2:9][C@@H:10]([F:17])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])=[C:6](Cl)[N:5]=[C:4]([C:19]2[CH:24]=[CH:23][C:22]([CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])=[CH:21][CH:20]=2)[N:3]=1.C(O)C.[O-2].[Mg+2].[H][H]>[C].[Pd].C1C=CC=CC=1.O>[F:17][C@@H:10]([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])[CH2:9][CH2:8][C:7]1[CH:6]=[N:5][C:4]([C:19]2[CH:20]=[CH:21][C:22]([CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])=[CH:23][CH:24]=2)=[N:3][CH:2]=1

Participants

8

Reactant 4

HCID 702EthanolHCID 6850729Magnesium monoxideHCID 54381008HCID 54381008, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 54011110HCID 54011110, compoundYield 69%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 241BenzeneSolventHCID 962WaterSolvent

Procedure

72 mg of palladium-carbon (palladium=about 5%), 372 mg (0.73 mM) of (S)-4,6-dichloro-(5-3-fluorononyl)-2-(4-decylphenyl)pyrimidine, 5 ml of 99%-ethanol, 118 mg (2.92 mM) of magnesium oxide and 0.3 ml of distilled water were placed in a two-necked round-bottomed flask and subjected to hydrogen addition for 5 hours at 60° C. After the reaction, benzene was added to the reaction mixture and the catalyst as removed from the reaction mixture, followed by distilling-off of the solvent and purification by thin-layer chromatography (eluent: benzene; Rf=0.5) to obtain 222 mg (0.50 mM) of (S)-5-(3-fluorononyl)-2-(4-decylphenyl)pyrimidine (crude product). The crude product was recrystallized from hexane to obtain an objective product (Yield: 69.2%).

Workup

  1. additionwas added to the reaction mixture
  2. customthe catalyst as removed from the reaction mixture
  3. distillationfollowed by distilling-off of the solvent and purification by thin-layer chromatography (eluent: benzene; Rf=0.5)

Sources & evidence

ORD record
ord-a27fcd1deac14fcdb5e06129e32227de
Source dataset
uspto-grants-1998_11
Patent number
US05830386

Reaction notes

Loading…