Methyl iodide → HCID 21912281, compound

HRID 1831705Notes

Reaction equation

HRID 1831705 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([CH3:8])[N:5]=[C:4]([NH:9][C:10]2[C:15]([CH3:16])=[CH:14][C:13]([CH3:17])=[CH:12][C:11]=2[CH3:18])[C:3]=1[CH3:19].[H-].[Na+].[CH3:22]I>C1COCC1>[Cl:1][C:2]1[N:7]=[C:6]([CH3:8])[N:5]=[C:4]([N:9]([CH3:22])[C:10]2[C:11]([CH3:18])=[CH:12][C:13]([CH3:17])=[CH:14][C:15]=2[CH3:16])[C:3]=1[CH3:19]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 21912049HCID 21912049, compound

Product 1

HCID 21912281HCID 21912281, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of (6-chloro-2,5-dimethylpyrimidin-4-yl)-(2,4,6-trimethylphenyl)-amine (276 mg, 1 mmol) in dry THF (2 ml) was treated with sodium hydride (60% in oil, 60 mg, 1.5 mmol) at room temperature. After stirring for 2 minutes, an excess of methyl iodide (0.5 ml) was added and the resulting mixture was stirred at room temperature for 20 minutes. The mixture was quenched with saturated ammonium chloride and extracted with ethyl acetate. The organic layer was separated, dried and concentrated to give a pale yellow solid (255 mg). 1H NMR (CDCl3) δ 6.85 (s, 2H), 3.26 (s, 3H), 2.50 (s, 3H), 2.27 (s, 3H), 2.03 (s, 6H), 1.39 (s, 3H) ppm.

Workup

  1. stirringthe resulting mixture was stirred at room temperature for 20 minutes
  2. customThe mixture was quenched with saturated ammonium chloride
  3. extractionextracted with ethyl acetate
  4. customThe organic layer was separated
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-c496a91fe0984e989ae31d0b91633031
Source dataset
uspto-grants-2006_06
Patent number
US07067664B1

Reaction notes

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