Triethylamine → Ethyl 2-(4-butoxyphenyl)pyrimidine-5-carboxylate

HRID 1195614Notes

Reaction equation

HRID 1195614 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7](Cl)=[N:8][C:9]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH2:19][CH2:20][CH2:21][CH3:22])=[CH:14][CH:13]=2)=[N:10][CH:11]=1)=[O:5])[CH3:2].C(N(CC)CC)C>C(OCC)(=O)C.[H][H].[Pd]>[CH2:1]([O:3][C:4]([C:6]1[CH:11]=[N:10][C:9]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH2:19][CH2:20][CH2:21][CH3:22])=[CH:14][CH:13]=2)=[N:8][CH:7]=1)=[O:5])[CH3:2]

Participants

6

Reactant 2

HCID 8471TriethylamineHCID 3614036HCID 3614036, compound

Product 1

HCID 13907408Ethyl 2-(4-butoxyphenyl)pyrimidine-5-carboxylateYield 80%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolventHCID 178418361HCID 178418361, compoundSolvent

Procedure

This compound (V) (3.3 g, 10 mmols) was dissolved in ethyl acetate (30 ml), followed by agitating the solution together with Pd/C (5%) (0.6 g) and triethylamine (1.0 g) in hydrogen atmosphere at room temperature for 3 hours, filtering off Pd/C, adding toluene (100 ml), washing the resulting fluid with 2N-hydrochloric acid (50 ml), washing it with water till the washing water became pH 7, drying the toluene phase over anhydrous magnesium sulfate, filtering off magnesium sulfate, concentrating under reduced pressure to obtain white crystals and recrystallizing the crystals from methanol to obtain ethyl-2-(4-butyloxyphenyl)-5-pyrimidinecarboxylate (VI) (2.4 g) (yield: 80%) having a melting point 99.1° C.

Workup

  1. filtrationfiltering off Pd/C
  2. additionadding toluene (100 ml)
  3. washwashing the resulting fluid with 2N-hydrochloric acid (50 ml)
  4. washwashing it with water till the washing water
  5. dry with materialdrying the toluene phase over anhydrous magnesium sulfate
  6. filtrationfiltering off magnesium sulfate
  7. concentrationconcentrating under reduced pressure
  8. customto obtain white crystals
  9. customrecrystallizing the crystals from methanol

Sources & evidence

ORD record
ord-df3701453e05455f9bfd5954154153f1
Source dataset
uspto-grants-1992_05
Patent number
US05112523

Reaction notes

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