Sodium hydride → 2-Chloro-4-dimethylamino-6-(3-thienylmethyloxy)pyridine

HRID 55134

Reaction equation

HRID 55134 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]([CH2:6][OH:7])=[CH:2]1.[H-].[Na+].[Cl:10][C:11]1[CH:16]=[C:15]([N:17]([CH3:19])[CH3:18])[CH:14]=[C:13](Cl)[N:12]=1>O1CCCC1>[Cl:10][C:11]1[CH:16]=[C:15]([N:17]([CH3:19])[CH3:18])[CH:14]=[C:13]([O:7][CH2:6][C:3]2[CH:4]=[CH:5][S:1][CH:2]=2)[N:12]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 123570Thiophene-3-methanolHCID 121751364-Pyridinamine, 2,6-dichloro-N,N-dimethyl-

Product 1

HCID 199574072-Chloro-4-dimethylamino-6-(3-thienylmethyloxy)pyridine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 3-thiophenemethanol (0.526 g, 0.0042×1.1 mol) in 10 ml of dry tetrahydrofuran, sodium hydride (0.335 g, (ca.60% in mineral oil), 0.0042×2.0 mol) was added. After the bubbling ceased, a solution of 2,6-dichloro-4-dimethylaminopyridine (0.8 g, 0.0042 mol) in 20 ml of dry tetrahydrofuran was added dropwise at room temperature.

Sources & evidence

ORD record
ord-294381b45af647be8b0a1ac7e5d7e5ef
Source dataset
uspto-grants-1997_04
Patent number
US05624942

Linked notes

Loading…