Imidazole → 4-(Tert-butyldimethylsilyloxymethyl)pyridinecarbonitrile

HRID 379878Notes

Reaction equation

HRID 379878 reaction equation
[C:1]([C:3]1[CH:8]=[C:7]([CH2:9][OH:10])[CH:6]=[CH:5][N:4]=1)#[N:2].N1C=CN=C1.[CH3:16][C:17]([Si:20](Cl)([CH3:22])[CH3:21])([CH3:19])[CH3:18]>CN(C=O)C.C(OCC)C>[Si:20]([O:10][CH2:9][C:7]1[CH:6]=[CH:5][N:4]=[C:3]([C:1]#[N:2])[CH:8]=1)([C:17]([CH3:19])([CH3:18])[CH3:16])([CH3:22])[CH3:21]

Participants

6

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 107253914-(Hydroxymethyl)pyridine-2-carbonitrile

Product 1

HCID 145414484-(Tert-butyldimethylsilyloxymethyl)pyridinecarbonitrile

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-cyano-4-hydroxymethylpyridine (step 1, 3.63 g, 27.06 mmol) in DMF (50 ml) were added imidazole (4.42 g, 64.95 mmol) and TBDMSCl (4.89 g, 32.47 mmol) at room temperature. After stirring for 1 h, the mixture was diluted with diethyl ether (300 ml), washed with water (100 ml×4), and dried (MgSO4). Removal of solvent gave the title compound. 1H-NMR (CDCl3) δ: 8.65 (1 H, d, J=5.1 Hz), 7.68 (1 H, s), 7.46 (1 H, d, J=4.9 Hz), 4.78 (2 H, s), 0.96 (9 H, s), 0.13 (6 H, s).

Workup

  1. washwashed with water (100 ml×4)
  2. dry with materialdried (MgSO4)
  3. customRemoval of solvent

Sources & evidence

ORD record
ord-483f7f8762f54b97b11ec9611bc15893
Source dataset
uspto-grants-2001_10
Patent number
US06300363B1

Reaction notes

Loading…