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

HRID 1370077Notes

Reaction equation

HRID 1370077 reaction equation
[C:1]([C:3]1[C:4]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[N:5][C:6]([NH:9][C:10]2[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][OH:18])=[CH:12][CH:11]=2)=[N:7][CH:8]=1)#[N:2].[C:25]1([CH3:35])[CH:30]=[CH:29][C:28]([S:31](Cl)(=[O:33])=[O:32])=[CH:27][CH:26]=1>>[C:1]([C:3]1[C:4]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[N:5][C:6]([NH:9][C:10]2[CH:11]=[CH:12][C:13]([CH2:16][CH2:17][O:18][S:31]([C:28]3[CH:29]=[CH:30][C:25]([CH3:35])=[CH:26][CH:27]=3)(=[O:33])=[O:32])=[CH:14][CH:15]=2)=[N:7][CH:8]=1)#[N:2]

Participants

3

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 185169192-(4-(2-Hydroxyethyl)phenylamino)-4-phenylpyrimidine-5-carbonitrile

Product 1

HCID 185168915-Cyano-4-phenyl-N-[4-(2-p-toluenesulphonyloxyethyl)phenyl]pyrimidine-2-amine

Procedure

5-Cyano-4-phenyl-N-[4-(2-p-toluenesulphonyloxyethyl)phenyl]pyrimidine-2-amine was prepared from 5-cyano-4-phenyl-N-[4-(2-hydroxyethyl)phenyl]pyrimidine-2-amine (3.30 g, 10.43 mmol) and 4-toluenesulphonylchloride (2.19 g, 11.47 mmol) as a pale yellow solid (3.91 g) m.p. 134-135°. δH (d6 DMSO) 8.69 (1H, s), 8.05 (2H, dd, J 6.0, 2.0 Hz), 7.72 (2H, d, J 8.3 Hz), 7.61-7.51 (6H, m), 7.29 (2H, d, J 8.1 Hz), 7.14 (2H, d, J 8.5 Hz), 4.21(2H, t, J 7.0 Hz), 2.95 (2H, t, J 7.0 Hz) and 2.41 (3H, s).

Sources & evidence

ORD record
ord-18f310b66138498f97481fd5a92026dd
Source dataset
uspto-grants-2003_06
Patent number
US06579983B1

Reaction notes

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