3-Pyridinemethanol → 2-Amino-4-phenyl-6-(3-pyridinylmethoxy)-3,5-pyridinedicarbonitrile

HRID 2264521Notes

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:28]=[N:29][CH:30]=[CH:31][CH:32]=1>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:28]=[N:29][CH:30]=[CH:31][CH:32]=2)[N:3]=1

Participants

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)] and 54 mg (0.48 mmol) of potassium tert-butoxide are dissolved together in 1.696 g (=1.5 ml, 15.55 mmol) of 3-hydroxymethylpyridine, and the mixture is stirred at 60° C. for about 16 h. The resulting suspension is acidified with two drops of glacial acetic acid. The product which crystallizes out is filtered off with suction, washed with water and dried under reduced pressure.

Workup

customThe product which crystallizes out
filtrationis filtered off with suction
washwashed with water
customdried under reduced pressure

Sources & evidence

ORD record: ord-705059d9258246a0b96d89126759683b
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07855219B2

Reaction notes

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