Imidazole → 3-{[(Tert-butyldimethylsilyl)oxy]methyl}pyridin-2-amine

HRID 374767Notes

Reaction equation

HRID 374767 reaction equation
[NH2:1][C:2]1[C:7]([CH2:8][OH:9])=[CH:6][CH:5]=[CH:4][N:3]=1.CN(C)C=O.N1C=CN=C1.Cl[Si:21]([CH3:27])([CH3:26])[C:22]([CH3:25])([CH3:24])[CH3:23]>O>[CH3:26][Si:21]([CH3:27])([C:22]([CH3:25])([CH3:24])[CH3:23])[O:9][CH2:8][C:7]1[C:2]([NH2:1])=[N:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 6228DimethylformamideHCID 28928tert-Butyldimethylsilyl chlorideHCID 11159325(2-Aminopyridin-3-yl)methanol

Product 1

HCID 189958043-{[(Tert-butyldimethylsilyl)oxy]methyl}pyridin-2-amineYield 93.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 6.2 parts of 2-amino-3-pyridinemethanol in 23.5 parts of N,N-dimethylformamide there were added 6.8 parts of 1H-imidazole and 7.5 parts of chlorodimethyl(1,1-dimethylethyl)silane. The whole was cooled for 10 min in an ice-bath and was stirred overnight at room temperature. The reaction mixture was diluted with 100 parts of water and the product was extracted with 1,1'-oxybisethane (2x). The combined extracts were washed with water and NaCl (sat.), dried, filtered and evaporated, yielding 11.1 parts (93.1% ) of 3-[[dimethyl(1,1-dimethylethyl)silyloxy]methyl]-2-pyridinamine (interm. 1).

Workup

  1. temperatureThe whole was cooled for 10 min in an ice-bath
  2. extractionthe product was extracted with 1,1'-oxybisethane (2x)
  3. washThe combined extracts were washed with water and NaCl (sat.)
  4. customdried
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-f3f70cfd08544cc6997f4a9264eb51db
Source dataset
uspto-grants-1996_01
Patent number
US05482943

Reaction notes

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