Methyl iodide → 5-(N-Boc-amino)-2-methoxy-4-methylpyridine

HRID 844444Notes

Reaction equation

HRID 844444 reaction equation
[CH2:1]([Li])CCC.CN(CCN(C)C)C.[C:14]([NH:21][C:22]1[CH:23]=[CH:24][C:25]([O:28][CH3:29])=[N:26][CH:27]=1)([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15].CI>CCCCCC.O>[C:14]([NH:21][C:22]1[C:23]([CH3:1])=[CH:24][C:25]([O:28][CH3:29])=[N:26][CH:27]=1)([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15]

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 8037N,N,N',N'-TetramethylethylenediamineHCID 2763103tert-Butyl (6-methoxypyridin-3-yl)carbamateHCID 178418339Butyllithium

Product 1

HCID 226125465-(N-Boc-amino)-2-methoxy-4-methylpyridine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8058HexaneSolvent

Procedure

41.7 ml of 1.6M n-butyllithium in hexane and 7.7 g of TMEDA are added, under nitrogen, to 5 g of 5-(N-Boc-amino)-2-methoxypyridine, at −60° C. The medium turns yellow. The mixture is left stirring for 4 hours, allowing the temperature to return to −10° C., and a pale yellow. precipitate forms. The mixture is recooled to −40° C. and 4.7 g of methyl iodide are then added. The medium is allowed to return to RT and is then poured into water and extracted with EtOAc, and the extracts are dried and evaporated. The residue is chromatographed on silica, eluting with cyclohexane/EtOAc (85/15; v/v).

Workup

  1. waitThe mixture is left
  2. customto return to −10° C.
  3. customis recooled to −40° C.
  4. customto return to RT
  5. extractionextracted with EtOAc
  6. customthe extracts are dried
  7. customevaporated
  8. customThe residue is chromatographed on silica
  9. washeluting with cyclohexane/EtOAc (85/15; v/v)

Sources & evidence

ORD record
ord-58ae9d71aa834a018ca78afe6de94408
Source dataset
uspto-grants-2002_04
Patent number
US06380230B1

Reaction notes

Loading…