Ethyl acetate hexane → HCID 178495596, compound

HRID 1166158Notes

Reaction equation

HRID 1166158 reaction equation
[N+](C1C=CC(C[O:9][C:10]2[N:15]=[CH:14][N:13]=[C:12]([O:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3/[C:23](=[CH:28]\[O:29][CH3:30])/[C:24]([O:26][CH3:27])=[O:25])[CH:11]=2)=CC=1)([O-])=O.[H][H].C(OCC)(=O)C.CCCCCC>C(O)C.[Pd]>[OH:9][C:10]1[N:15]=[CH:14][N:13]=[C:12]([O:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2/[C:23](=[CH:28]\[O:29][CH3:30])/[C:24]([O:26][CH3:27])=[O:25])[CH:11]=1

Participants

6

Reactant 3

HCID 21226206Ethyl acetate hexaneHCID 69884992HCID 69884992, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 178495596HCID 178495596, compoundYield 51.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

(E)-Methyl 2-[2-(6-(4-nitrobenzyloxy)pyrimidin-4-yloxy)phenyl]-3-methoxypropenoate (1.4 g) in ethanol (30 ml) in the presence of 5% Pd/C catalyst (300 mg) was treated with hydrogen at 1 atmosphere pressure. After 90 minutes, the reaction mixture was filtered and evaporated to give a yellow oil. Chromatography (eluent ethyl acetate-hexane, 95:5) afforded (E)-methyl 2-[2-(6-hydroxypyrimidin-4-yloxy)phenyl]-3-methoxypropenoate (500 mg) as a pale yellow solid; m.p. 168-170° C.; 1H NMR: δ 3.80(3H,s), 5.65(1H,s), 7.15(1H,d), 7.3(3H,m), 7.50(1H,s), 7.95(1H,s) ppm; IR maximum: 1680 cm−1; mass spectrum m/e 302 (M+).

Workup

  1. filtrationthe reaction mixture was filtered
  2. customevaporated
  3. customto give a yellow oil

Sources & evidence

ORD record
ord-d872872c37984ccf8c055fa279761427
Source dataset
uspto-grants-2003_09
Patent number
US06613773B2

Reaction notes

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