Triethylamine → HCID 178472480, compound

HRID 1516151Notes

Reaction equation

HRID 1516151 reaction equation
[CH2:1]([O:3][C:4]([C@H:6]1[CH2:11][CH2:10][C@H:9]([O:12][C:13]2[CH:18]=[C:17](Cl)[N:16]=[CH:15][N:14]=2)[CH2:8][CH2:7]1)=[O:5])[CH3:2].C(N(CC)CC)C>C(OCC)(=O)C.[Pd]>[CH2:1]([O:3][C:4]([C@H:6]1[CH2:11][CH2:10][C@H:9]([O:12][C:13]2[CH:18]=[CH:17][N:16]=[CH:15][N:14]=2)[CH2:8][CH2:7]1)=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 178472463HCID 178472463, compound

Product 1

HCID 178472480HCID 178472480, compoundYield 99.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To an argon purged solution of cis/trans-4-(6-chloro-pyrimidin-4-yloxy)-cyclohexanecarboxylic acid ethyl ester (1:1) (1.05 g, 3.69 mmol) and triethylamine (0.52 ml, 3.69 mmol) in ethyl acetate (37 ml) was added palladium on charcoal 10% (0.078 g). The reaction mixture was purged with hydrogen gas and stirred under an atmosphere of hydrogen gas for 16 h at room temperature. The catalyst and the ammonium salts were removed by filtration over Decalite. The filtrate was concentrated in vacuo to give the title compound (0.92 g) as light yellow oil in quantitative yield.

Workup

  1. customThe reaction mixture was purged with hydrogen gas
  2. customThe catalyst and the ammonium salts were removed by filtration over Decalite
  3. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-7e3257c9a305485fbb568bbd9ce15b46
Source dataset
uspto-grants-2012_07
Patent number
US08227458B2

Reaction notes

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