HCID 50996264, compound → HCID 50997510, compound

HRID 1399571Notes

Reaction equation

HRID 1399571 reaction equation
[CH3:1][C:2]1[C:7]([CH:8]([CH2:13][CH2:14][CH3:15])[C:9]([O:11][CH3:12])=[O:10])=[C:6]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[N:5]=[C:4](/[CH:22]=[CH:23]/[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[N:3]=1>C(O)C.[Pd]>[CH3:1][C:2]1[C:7]([CH:8]([CH2:13][CH2:14][CH3:15])[C:9]([O:11][CH3:12])=[O:10])=[C:6]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[N:5]=[C:4]([CH2:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[N:3]=1

Participants

4

Reactant 1

HCID 50996264HCID 50996264, compound

Product 1

HCID 50997510HCID 50997510, compoundYield 99.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a suspension of (E)-methyl 2-(4-methyl-6-phenyl-2-styrylpyrimidin-5-yl)pentanoate (91 mg; 0.235 mmol) in ethanol (2 mL) was added 10% Pd/C. The solution was deoxygenated and back filled with a nitrogen atmosphere twice. The solution was then degassed, back filled with hydrogen gas and allowed to react at room temperature overnight. The reaction mixture was filtered using a syringe filter and the solvent was removed under reduced pressure. The crude material was purified by flash chromatography on silica gel using a linear gradient of ethylacetate (5-30%) in heptane to give 91 mg of the title compound which was immediately used in the next step. ESI/APCI(+): 389 (M+H).

Workup

  1. customThe solution was deoxygenated
  2. additionback filled with a nitrogen atmosphere twice
  3. customThe solution was then degassed
  4. additionback filled with hydrogen gas
  5. customto react at room temperature overnight
  6. filtrationThe reaction mixture was filtered
  7. filtrationfilter
  8. customthe solvent was removed under reduced pressure
  9. customThe crude material was purified by flash chromatography on silica gel using a linear gradient of ethylacetate (5-30%) in heptane

Sources & evidence

ORD record
ord-d85d44ca8a434208a5eec9de4a1ac90f
Source dataset
uspto-grants-2014_12
Patent number
US08906906B2

Reaction notes

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