2,6-Lutidine → 2-Methylpentane

HRID 347746Notes

Reaction equation

HRID 347746 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[CH:5]=[CH:4][N:3]=1.[NH2:9][C:10]1[CH:19]=[CH:18][CH:17]=[CH:16][C:11]=1[C:12]([O:14][CH3:15])=[O:13].N1C(C)=CC=CC=1C>C(O)CCC>[CH3:18][CH2:19][CH2:10][CH:11]([CH3:16])[CH3:12].[Cl:1][C:2]1[N:7]=[C:6]([NH:9][C:10]2[CH:19]=[CH:18][CH:17]=[CH:16][C:11]=2[C:12]([O:14][CH3:15])=[O:13])[CH:5]=[CH:4][N:3]=1

Participants

6

Reactant 3

HCID 79372,6-LutidineHCID 8635Methyl AnthranilateHCID 775312,4-Dichloropyrimidine

Product 2

HCID 78922-MethylpentaneHCID 1713300methyl 2-[(2-chloropyrimidin-4-yl)amino]benzoate

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
120 °C

Procedure

2,4-Dichloropyrimidine (596 mg, 4 mmol), methyl 2-aminobenzoate (517 ml, 4 mmol) and 2,6-lutidine (465 ml, 4 mmol) were dissolved in n-butanol (20 ml) with stirring. The reaction mixture was heated to 120° C. for 24 hours, allowed to cool to ambient temperature and evaporated onto silica (3 ml). The residue was purified by column chromatography eluting with EtOAc (0–20%): isohexane to give the title product as a colourless solid on evaporation (137 mg, 13%). NMR (CDCl3, 300 MHz): 3.97 (s, 3H), 6.63 (d, 1H), 7.09 (t, 1H) 7.61 (m, 1H), 8.05 (d, 1H), 8.19 (d, 1H), 8.74 (d, 1H); m/z: (ES+) 264.3 (MH+).

Workup

  1. temperatureto cool to ambient temperature
  2. customevaporated onto silica (3 ml)
  3. customThe residue was purified by column chromatography
  4. washeluting with EtOAc (0–20%)

Sources & evidence

ORD record
ord-193752760095427e95b3b41d483b39b2
Source dataset
uspto-grants-2007_02
Patent number
US07176212B2

Reaction notes

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