2-(2,6-Diethylphenyl)-4-methoxy-6-methyl-5-(1-propylbutenyl)pyrimidine → 2-(2,6-Diethylphenyl)-4-methoxy-6-methyl-5-(1-propylbutyl)pyrimidine

HRID 1455768Notes

Reaction equation

HRID 1455768 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH2:9][CH3:10])[C:4]=1[C:11]1[N:16]=[C:15]([O:17][CH3:18])[C:14]([C:19]([CH2:23][CH2:24][CH3:25])=[CH:20][CH2:21][CH3:22])=[C:13]([CH3:26])[N:12]=1)[CH3:2]>CO.[Pd]>[CH2:9]([C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([CH2:1][CH3:2])[C:4]=1[C:11]1[N:16]=[C:15]([O:17][CH3:18])[C:14]([CH:19]([CH2:20][CH2:21][CH3:22])[CH2:23][CH2:24][CH3:25])=[C:13]([CH3:26])[N:12]=1)[CH3:10]

Participants

4

Reactant 1

HCID 665898042-(2,6-Diethylphenyl)-4-methoxy-6-methyl-5-(1-propylbutenyl)pyrimidine

Product 1

HCID 575314712-(2,6-Diethylphenyl)-4-methoxy-6-methyl-5-(1-propylbutyl)pyrimidine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 2-(2,6-diethylphenyl)-4-methoxy-6-methyl-5-(1-propylbutenyl)pyrimidine (100 mg) in MeOH is hydrogenated over Pd-C at 50 psi for 18 h. The catalyst is removed by filtration and the filtrate is concentrated to afford the title compound. 1H NMR (300 MHz, CDCl3): δ 7.24-7.29 (m, 1H), 7.13 (d, J=8 Hz, 2H), 3.91 (s, 3H), 2.51 (s, 3H), 2.41 (q, J=7.5 Hz, 4H), 2.38-2.45 (m, 8H), 1.58-1.82 (m, 3H), 1.14-1.44 (m, 2H), 1.08 (q, J=7.5, 6.6 Hz, 6H) 0.89 (t, J=7.5 Hz, 6H); LC-MS found 355 (MH+).

Workup

  1. customThe catalyst is removed by filtration
  2. concentrationthe filtrate is concentrated

Sources & evidence

ORD record
ord-985122f530b7459081f0148c1c79dd8d
Source dataset
uspto-grants-2009_01
Patent number
US07482350B2

Reaction notes

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