Chlorotrimethylsilane → 2-[N,N-bis(trimethylsilyl)amino]-6-methylpyridine

HRID 1982676Notes

Reaction equation

HRID 1982676 reaction equation
CCCCCC.C([Li])CCC.[NH2:12][C:13]1[N:18]=[C:17]([CH3:19])[CH:16]=[CH:15][CH:14]=1.[CH3:20][Si:21](Cl)([CH3:23])[CH3:22]>O1CCCC1>[CH3:20][Si:21]([CH3:23])([CH3:22])[N:12]([C:13]1[N:18]=[C:17]([CH3:19])[CH:16]=[CH:15][CH:14]=1)[Si:21]([CH3:23])([CH3:22])[CH3:20]

Participants

6

Reactant 4

HCID 6397ChlorotrimethylsilaneHCID 8058HexaneHCID 157652-Amino-6-methylpyridineHCID 178418339Butyllithium

Product 1

HCID 112305162-[N,N-bis(trimethylsilyl)amino]-6-methylpyridineYield 77.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A 15% n-hexane solution (636 g.) of n-butyllithium was added to a solution of 6-amino-2-methylpyridine (64.8 g.) in tetrahydrofuran (500 ml.) at -20° to -30° C. over one hour, and stirred at -8° to -10° C. for 30 minutes. To the solution was added trimethylsilylchloride (161.7 g.) at -15° to -5° C. over 40 minutes, and the resultant solution was stirred at room temperature overnight. The solution was filtered through by a column packed with silica gel (180 g.), washed with tetrahydrofuran and then the filtrate was concentrated under reduced pressure. The residue was purified by fractional distillation to give 6-[N,N-bis(trimethylsilyl)amino]-2-methylpyridine (117.6 g.), b.p. 95° to 97° C./5-6 mm.

Workup

  1. filtrationThe solution was filtered through by a column
  2. washwashed with tetrahydrofuran
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. distillationThe residue was purified by fractional distillation

Sources & evidence

ORD record
ord-010210f9c82147ff9a3eb2da28614d39
Source dataset
uspto-grants-1986_06
Patent number
US04596869

Reaction notes

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