4-Toluenesulfonyl chloride → 5-cyano4phenyl-N-[4-(2-p-toluenesulphonyloxyethoxy)phenyl]pyrimidine-2-amine

HRID 1370079Notes

Reaction equation

HRID 1370079 reaction equation
[C:1]([C:3]1[C:4]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[N:5][C:6]([NH:9][C:10]2[CH:15]=[CH:14][C:13]([O:16][CH2:17][CH2:18][OH:19])=[CH:12][CH:11]=2)=[N:7][CH:8]=1)#[N:2].[C:26]1([CH3:36])[CH:31]=[CH:30][C:29]([S:32](Cl)(=[O:34])=[O:33])=[CH:28][CH:27]=1.C1(C(=O)C(C#N)=CN(C)C)C=CC=CC=1.[N+]([O-])([O-])=O.OCCOC1C=CC(NC(N)=[NH2+])=CC=1.[OH-].[Na+]>>[C:1]([C:3]1[C:4]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[N:5][C:6]([NH:9][C:10]2[CH:11]=[CH:12][C:13]([O:16][CH2:17][CH2:18][O:19][S:32]([C:29]3[CH:30]=[CH:31][C:26]([CH3:36])=[CH:27][CH:28]=3)(=[O:34])=[O:33])=[CH:14][CH:15]=2)=[N:7][CH:8]=1)#[N:2].[C:1]([C:3]1[C:4]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[N:5][C:6]([NH:9][C:10]2[CH:11]=[CH:12][C:13]([O:16][CH2:17][CH2:18][OH:19])=[CH:14][CH:15]=2)=[N:7][CH:8]=1)#[N:2]

Participants

7

Reactant 5

HCID 73974-Toluenesulfonyl chlorideHCID 14798Sodium HydroxideHCID 38455902-[(Dimethylamino)methylene]-3-oxo-3-phenylpropanenitrileHCID 185169505-cyano-4-phenyl-N-[4-(2-hydroxyethoxy)phenyl]pyrimidine-2-amineHCID 178512445HCID 178512445, compound

Product 2

HCID 185168615-cyano4phenyl-N-[4-(2-p-toluenesulphonyloxyethoxy)phenyl]pyrimidine-2-amineHCID 185169505-cyano-4-phenyl-N-[4-(2-hydroxyethoxy)phenyl]pyrimidine-2-amine

Procedure

5-cyano-4-phenyl-N-[4-(2-p-toluenesulphonyloxyethoxy)phenyl]pyrimidine-2-amine was prepared from 5-cyano-4-phenyl-N-[4-(2-hydroxy-ethoxy)phenyl]pyrimidine-2-amine (1.42 g,4.28 mmol) and 4-toluene-sulphonyl chloride (1.23 g, 6.4 mmol) as a yellow solid, m.p. 147°. δH (CDCl3) 8.67 (1H, s), 8.05-8.03 (2H, m), 7.83 (2H, dd, J 6.5, 1.8 Hz), 7.58-7.49 (6H, m), 7.35 (2H, dd, J 8.6, 0.9 Hz), 6.83 (2H, d, J 0.9 Hz), 4.38-4.36 (2H, m), 4.18-4.16 (2H, m) and 2.45 (3H, s). 5-cyano-4-phenyl-N-[4-(2-hydroxyethoxy)phenyl]pyrimidine-2-amine was prepared from 1-phenyl-2-cyano-3-dimethylaminopropen-1-one (1.41 g, 7.0 mmol), 4-(2-hydroxy-ethoxy) phenylguanidinium nitrate (2.0 g, 7.7 mmol) and sodium hydroxide (340 mg, 8.4 mmol) to give a yellow solid (1.54 g), m.p. 151°. δH (CDCl) 8.67 (1H, s), 8.04 (2H, d, J 7.7 Hz), 7.58-7.52 (5H, m), 7.45 (1H, s), 6.95 (2H, dd, J 6.7,2.3 Hz), 4.12-4.09 (2H, m), 4.00-3.97 (2H, m) and 2.05-2.01 (1H, m).

Sources & evidence

ORD record
ord-a4a2d494229345cab06661c24d3a8968
Source dataset
uspto-grants-2003_06
Patent number
US06579983B1

Reaction notes

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