Imidazole → HCID 178455437, compound

HRID 1643561Notes

Reaction equation

HRID 1643561 reaction equation
N[C:2]1N=[CH:6][C:5]([CH2:8]O)=[CH:4][CH:3]=1.[CH3:10][C:11]([Si:14](Cl)(C)C)([CH3:13])[CH3:12].[NH:18]1C=CN=C1.[OH2:23].[CH3:24][N:25]([CH:27]=O)C>>[C:11]([SiH2:14][O:23][C:5]([CH3:8])([CH3:6])[C:4]1[CH:3]=[CH:2][C:24]([NH2:18])=[N:25][CH:27]=1)([CH3:13])([CH3:12])[CH3:10]

Participants

6

Reactant 5

HCID 795ImidazoleHCID 962WaterHCID 6228DimethylformamideHCID 28928tert-Butyldimethylsilyl chlorideHCID 2794829(6-Aminopyridin-3-yl)methanol

Product 1

HCID 178455437HCID 178455437, compoundYield 76%

Procedure

A mixture of (6-aminopyridin-3-yl)methanol (1.76 g, 14.2 mmol), TBDMSCl (2.18 g, 14.5 mmol), and imidazole (2.90 g, 42.6 mmol) in 20 mL DMF was stirred at room temperature for 2 hr. H2O was added, extracted with 3×EtOAc. The combined organic layer was washed with 2×H2O, dried with Na2SO4, and concentrated to give an off-white solid (2.57 g, 76% yield). 1H NMR (400 MHz, CDCl3)) δ 8.01 (d, J=1.77 Hz, 1 H) 7.44 (dd, J=8.34, 2.27 Hz, 1 H) 6.50 (d, J=8.34 Hz, 1 H) 4.60 (s, 2 H) 4.38 (br. s., 2 H) 0.93 (s, 9H) 0.11 (s, 6 H); LCMS for C12H22N2OSi m/z 239.00 (M+H).

Workup

  1. extractionextracted with 3×EtOAc
  2. washThe combined organic layer was washed with 2×H2O
  3. dry with materialdried with Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-2059664429df4f84955672065d0c47a0
Source dataset
uspto-grants-2012_02
Patent number
US08119624B2

Reaction notes

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