(-)-5-Decyloxy-2-[4-(6-hydroxyheptynyl)phenyl]pyrimidine → (-)-5-Decyloxy-2-[4-(6-hydroxyheptyl)phenyl]pyrimidine

HRID 1956085Notes

Reaction equation

HRID 1956085 reaction equation
[CH2:1]([O:11][C:12]1[CH:13]=[N:14][C:15]([C:18]2[CH:23]=[CH:22][C:21]([C:24]#[C:25][CH2:26][CH2:27][CH2:28][CH:29]([OH:31])[CH3:30])=[CH:20][CH:19]=2)=[N:16][CH:17]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].[H][H]>[Pd].C1COCC1>[CH2:1]([O:11][C:12]1[CH:13]=[N:14][C:15]([C:18]2[CH:19]=[CH:20][C:21]([CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH:29]([OH:31])[CH3:30])=[CH:22][CH:23]=2)=[N:16][CH:17]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]

Participants

5

Reactant 2

HCID 19437556(-)-5-Decyloxy-2-[4-(6-hydroxyheptynyl)phenyl]pyrimidineHCID 178418361HCID 178418361, compound

Product 1

HCID 19437524(-)-5-Decyloxy-2-[4-(6-hydroxyheptyl)phenyl]pyrimidineYield 101.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

In a reactor equipped with a stirrer and a thermometer, (-)-5-decyloxy-2-[4-(6-hydroxyheptynyl)phenyl]pyrimidine (4.0 g), 5% Pd/C (0.5 g) and THF (50 ml) are charged, and the mixture is reacted at room temperature for 17 hours in a hydrogen atmosphere under ordinary pressure. After filtrating the catalyst off, the reaction mixture is evaporated under reduced pressure. A resulting residue is purified by silica gel column chromatography (eluent: toluene-ethyl acetate) to obtain (-)-5-decyloxy-2-[4-(6-hydroxyheptyl)phenyl]pyrimidine (4.11 g). [α]D =-2.8° (c=1.055, CHCl3).

Workup

  1. customIn a reactor equipped with a stirrer
  2. filtrationAfter filtrating the catalyst off, the reaction mixture
  3. customis evaporated under reduced pressure
  4. customA resulting residue is purified by silica gel column chromatography (eluent: toluene-ethyl acetate)

Sources & evidence

ORD record
ord-5b4f718801674fe6a17426b15d4feadf
Source dataset
uspto-grants-1998_07
Patent number
US05779934

Reaction notes

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