Ethanol → 5-Methoxy-2-(4-octylphenyl)pyrimidine

HRID 1164764Notes

Reaction equation

HRID 1164764 reaction equation
Cl[C:2]1[C:7]([O:8][CH3:9])=[C:6](Cl)[N:5]=[C:4]([C:11]2[CH:16]=[CH:15][C:14]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])=[CH:13][CH:12]=2)[N:3]=1.C(O)C.O.C(N(CC)CC)C>[H][H].[Pd]>[CH3:9][O:8][C:7]1[CH:6]=[N:5][C:4]([C:11]2[CH:16]=[CH:15][C:14]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])=[CH:13][CH:12]=2)=[N:3][CH:2]=1

Participants

7

Reactant 4

HCID 702EthanolHCID 962WaterHCID 8471TriethylamineHCID 147447634,6-Dichloro-5-methoxy-2-(4-octylphenyl)pyrimidine

Product 1

HCID 147447645-Methoxy-2-(4-octylphenyl)pyrimidine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 178418361HCID 178418361, compoundSolvent

Procedure

To 4,6-dichloro-5-methoxy-2-(4-octylphenyl)pyrimidine (74.2 g, 0.202 mol) were added ethanol (310 ml), water (15.5 ml), 5% Pd-activated carbon (5.7 g) and triethylamine (61.3 g, 0.606 mol), followed by agitating the mixture at about 40° C. in hydrogen current, filtering off the Pd-activated carbon adding toluene, sufficiently washing the mixture with 2N-NaOH aqueous solution, further washing it with water, distilling off toluene and recrystallizing the residue from ethanol (70 ml) to obtain 5-methoxy-2-(4-octylphenyl)pyrimidine in the form of colorless acicular crystals (54.9 g) having a m.p. of 40.1-41.8° C.

Workup

  1. filtrationfiltering off the Pd-activated carbon
  2. additionadding toluene
  3. washsufficiently washing the mixture with 2N-NaOH aqueous solution
  4. washfurther washing it with water
  5. distillationdistilling off toluene
  6. customrecrystallizing the residue from ethanol (70 ml)

Sources & evidence

ORD record
ord-53e4d6b559f24fbaa3fae52957902079
Source dataset
uspto-grants-1990_03
Patent number
US04906400

Reaction notes

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