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 1091950Notes

Reaction equation

HRID 1091950 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-1a7e23caa6454430916737a139d6999d
Source dataset
uspto-grants-2012_03
Patent number
US08129395B2

Reaction notes

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