4-Hydroxymethylpyridine → HCID 9880443, compound

HRID 2264522Notes

Reaction equation

HRID 2264522 reaction equation
[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:5]([C:16]#[N:17])=[C:4](Cl)[N:3]=1.CC(C)([O-])C.[K+].[OH:25][CH2:26][C:27]1[CH:32]=[CH:31][N:30]=[CH:29][CH:28]=1>CS(C)=O.C(O)(=O)C>[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:5]([C:16]#[N:17])=[C:4]([O:25][CH2:26][C:27]2[CH:32]=[CH:31][N:30]=[CH:29][CH:28]=2)[N:3]=1

Participants

6

Reactant 3

HCID 114724-HydroxymethylpyridineHCID 27867132-amino-6-chloro-4-phenylpyridine-3,5-dicarbonitrileHCID 23665647Potassium tert-butoxide

Product 1

HCID 9880443HCID 9880443, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
60 °C

Procedure

102 mg (0.4 mmol) of 2-amino-6-chloro-4-phenyl-3,5-pyridinedicarbonitrile [Quintela et al., Heterocycles 38, 1299-1305 (1994)] are, together with 54 mg (0.48 mmol) of potassium tert-butoxide and 131 mg (1.2 mmol) of 4-hydroxymethylpyridine, dissolved in 1.5 ml of DMSO, and the mixture is stirred at 60° C. for about 16 h. The reaction mixture is acidified with two drops of glacial acetic acid. The solution is purified by preparative HPLC on reversed-phase silica gel (gradient: water+0.1% formic acid/acetonitrile 90:1010:90 in 12 minutes).

Workup

  1. customThe solution is purified by preparative HPLC on reversed-phase silica gel (gradient: water+0.1% formic acid/acetonitrile 90:1010:90 in 12 minutes)

Sources & evidence

ORD record
ord-e6e0a98708c4441c8261e00f8d118271
Source dataset
uspto-grants-2010_12
Patent number
US07855219B2

Reaction notes

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