4-Toluenesulfonyl chloride → HCID 18516858, compound

HRID 1370080Notes

Reaction equation

[C:1]([C:3]1[C:4]([C:20]2[S:21][CH:22]=[CH:23][CH:24]=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: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:20]2[S:21][CH:22]=[CH:23][CH:24]=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: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

Reactant 2

HCID 73974-Toluenesulfonyl chloride

HCID 18516982HCID 18516982, compound

Product 1

HCID 18516858HCID 18516858, compound

Procedure

5cyano-N-[4-(2-p-toluenesulphonyloxyethoxy)phenyl]-4-thien-2-ylpyrimidin-2-amine was prepared from 5-cyano-N-[4-(2-hydroxyethoxy)-phenyl]-4-thien-2-ylpyrimidine-2-amine (8.02 g, 23.7 mmol) and 4-toluene-sulphonylchloride (9.0 g, 47.4 mmol) to give a yellow solid (4.97 g), m.p. 160°. δH (d6 DMSO) 10.32 (1H, s), 8.84 (1H, s), 8.26 (1H, d, J 3.9 Hz), 7.99 (1H, d, J 5.0 Hz), 7.80 (2H, d, J 8.3 Hz), 7.64 (2H, m), 7.47 (2H, d, J 8.3hz), 7.33 (1H, t, J 4.5 Hz), 6.85 (2H, d, J 9.0 Hz), 4.33 (2H, t, J 4.0 Hz), 4.15 (2H, m) and 2.41 (3H, s).

Sources & evidence

ORD record: ord-aad5e9efc5e542cbbfe77aa2cb1ad2cc
Source dataset: uspto-grants-2003_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06579983B1

Reaction notes

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