[3-(Hydroxymethyl)phenyl]boronic acid → 1-(2-{4-(5-Chlorothiophen-2-yl)-5-[3-(hydroxymethyl)phenyl]pyrimidin-2-ylamino}ethyl)-5,5-dimethylimidazolidine-2,4-dione

HRID 507591Notes

Reaction equation

HRID 507591 reaction equation
Br[C:2]1[C:3]([C:20]2[S:21][C:22]([Cl:25])=[CH:23][CH:24]=2)=[N:4][C:5]([NH:8][CH2:9][CH2:10][N:11]2[C:15]([CH3:17])([CH3:16])[C:14](=[O:18])[NH:13][C:12]2=[O:19])=[N:6][CH:7]=1.[OH:26][CH2:27][C:28]1[CH:29]=[C:30](B(O)O)[CH:31]=[CH:32][CH:33]=1>>[Cl:25][C:22]1[S:21][C:20]([C:3]2[C:2]([C:32]3[CH:31]=[CH:30][CH:29]=[C:28]([CH2:27][OH:26])[CH:33]=3)=[CH:7][N:6]=[C:5]([NH:8][CH2:9][CH2:10][N:11]3[C:15]([CH3:17])([CH3:16])[C:14](=[O:18])[NH:13][C:12]3=[O:19])[N:4]=2)=[CH:24][CH:23]=1

Participants

3

Reactant 2

HCID 2734662[3-(Hydroxymethyl)phenyl]boronic acidHCID 602044701-{2-[5-Bromo-4-(5-chlorothiophen-2-yl)pyrimidin-2-ylamino]ethyl}-5,5-dimethylimidazolidine-2,4-dione

Product 1

HCID 602044911-(2-{4-(5-Chlorothiophen-2-yl)-5-[3-(hydroxymethyl)phenyl]pyrimidin-2-ylamino}ethyl)-5,5-dimethylimidazolidine-2,4-dione

Procedure

The title compound was prepared from 1-{2-[5-bromo-4-(5-chlorothiophen-2-yl)pyrimidin-2-ylamino]ethyl}-5,5-dimethylimidazolidine-2,4-dione and 3-(hydroxymethyl)phenylboronic acid in a manner analogous to Example 269. MS (M+H)+ 472.

Sources & evidence

ORD record
ord-7865409ed0114967b9a842fe0206b016
Source dataset
uspto-grants-2010_08
Patent number
US07786132B2

Reaction notes

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