6-(2-Pyrimidinyl)-5-hexyn-1-ol → 6-(Pyrimidin-2-yl)hexan-1-ol

HRID 1886012Notes

Reaction equation

HRID 1886012 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[N:3][C:2]=1[C:7]#[C:8][CH2:9][CH2:10][CH2:11][CH2:12][OH:13]>C(O)C.[Pd]>[N:1]1[CH:6]=[CH:5][CH:4]=[N:3][C:2]=1[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][OH:13]

Participants

4

Reactant 1

HCID 198767486-(2-Pyrimidinyl)-5-hexyn-1-ol

Product 1

HCID 198767736-(Pyrimidin-2-yl)hexan-1-olYield 29.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent2×

Procedure

A solution of 6-(2-pyrimidinyl)-5-hexynol (3.09 g) in ethanol (100 ml) was added to a pre-hydrogenated suspension of 10% palladium on charcoal (1.05 g) in ethanol (50 ml) and hydrogenated at room temperature and pressure, filtered and evaporated in vacuo. The residual oil was purified by FCC eluting with ether and System C (99:1-85:15) to give the title compound as a pale yellow oil (0.93 g).

Workup

  1. filtrationpressure, filtered
  2. customevaporated in vacuo
  3. customThe residual oil was purified by FCC
  4. washeluting with ether and System C (99:1-85:15)

Sources & evidence

ORD record
ord-4ab2a6f5eed9480ca3382287c4069849
Source dataset
uspto-grants-1992_09
Patent number
US05149698

Reaction notes

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