Triethylamine → 6-({[Tert-butyl(dimethyl)silyl]oxy}methyl)pyridin-2-amine

HRID 2374461Notes

Reaction equation

HRID 2374461 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([CH2:8][OH:9])[CH:5]=[CH:4][CH:3]=1.[C:10]([Si:14](Cl)([CH3:16])[CH3:15])([CH3:13])([CH3:12])[CH3:11].C(N(CC)CC)C>ClCCl>[Si:14]([O:9][CH2:8][C:6]1[N:7]=[C:2]([NH2:1])[CH:3]=[CH:4][CH:5]=1)([C:10]([CH3:13])([CH3:12])[CH3:11])([CH3:16])[CH3:15]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chlorideHCID 111826066-Amino-2-pyridinemethanol

Product 1

HCID 211322306-({[Tert-butyl(dimethyl)silyl]oxy}methyl)pyridin-2-amineYield 76.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of dichloromethane (15 mL) was added (6-aminopyridin-2-yl)methanol (0.72 g, 5.8 mmol), tert-butyl(chloro)dimethylsilane (1.05 g, 6.95 mmol) and triethylamine (1.05 mL, 7.53 mmol). The mixture was stirred for 24 h and washed with saturated sodium bicarbonate (2×30 mL) and aqueous hydrochloric acid (2×30 mL, 0.1 N). The organic layer was dried over anhydrous Na2SO4, filtered, and concentrated in vacuo. Purification was done using silica gel chromatography eluting with hexane: ethyl acetate (1:1) and fractions were combined and concentrated to afford the titled product as a white solid (1.06 g, 70%). HPLC: Rt 2.58 min. (96.5% area). 1H NMR (400 MHz, CDCl3), δ: 7.34 (t, J=7.6 Hz, 1H), 6.75 (d, J=7.6 Hz, 1H), 6.25 (d, J=8.1 Hz, 1H), 4.54 (s, 2H), 4.27 (bs, 2H), 0.84 (s, 9H), 0.11 (s, 6H); LRMS (ESI): m/z: 239.2.

Workup

  1. washwashed with saturated sodium bicarbonate (2×30 mL) and aqueous hydrochloric acid (2×30 mL, 0.1 N)
  2. dry with materialThe organic layer was dried over anhydrous Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customPurification
  6. washeluting with hexane: ethyl acetate (1:1) and fractions
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-9b43932bf58242148eac62d956b4faa0
Source dataset
uspto-grants-2008_12
Patent number
US07462634B2

Reaction notes

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