Sodium Hydroxide → 2-(4-(2-Hydroxyethyl)phenylamino)-4-phenylpyrimidine-5-carbonitrile

HRID 1370078Notes

Reaction equation

HRID 1370078 reaction equation
[C:1]1([C:7](=O)[C:8]([C:13]#N)=[CH:9][N:10](C)C)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N+]([O-])([O-])=O.[OH:20][CH2:21][CH2:22][C:23]1[CH:28]=[CH:27][C:26]([NH:29][C:30]([NH2:32])=[NH2+:31])=[CH:25][CH:24]=1.[OH-].[Na+]>>[C:9]([C:8]1[C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[N:31][C:30]([NH:29][C:26]2[CH:25]=[CH:24][C:23]([CH2:22][CH2:21][OH:20])=[CH:28][CH:27]=2)=[N:32][CH:13]=1)#[N:10]

Participants

4

Reactant 3

HCID 14798Sodium HydroxideHCID 38455902-[(Dimethylamino)methylene]-3-oxo-3-phenylpropanenitrileHCID 178512438HCID 178512438, compound

Product 1

HCID 185169192-(4-(2-Hydroxyethyl)phenylamino)-4-phenylpyrimidine-5-carbonitrile

Procedure

5-Cyano-4-phenyl-N-[4-(2-hydroxyethyl)phenyl]pyrimidine-2-amine was prepared from 1-phenyl-2-cyano-3-dimethylaminopropen-1-one (4.0 g, 20 mmol), 4-(2-hydroxyethyl)phenyl-guanidinium nitrate (4.24 g,20 mmol) and sodium hydroxide (800 mg, 20.0 mmol) as a yellow solid (3.50 g), m.p. 142-143°. δH (CDCl3) 8.68 (1H, s), 8.03 (2H, dd, J 6.0, 2.0 Hz), 7.66 (1H, bs), 7.59-7.51 (5H, m), 7.23 (2H, m), 3.88 (2H, t, J 6.5 Hz), 2.87 (2H, t, J 6.5 Hz) and 1.62 (2H, bs).

Sources & evidence

ORD record
ord-4fc222f5ba4c4a43842285c86f02198f
Source dataset
uspto-grants-2003_06
Patent number
US06579983B1

Reaction notes

Loading…