2-Thiopheneboronic acid → (R)-2-(2-chloro-5-(2-thienyl)pyrimidine-4-ylamino)butan-1-ol

HRID 1169732Notes

Reaction equation

HRID 1169732 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([NH:8][C@H:9]([CH2:12][CH3:13])[CH2:10][OH:11])[C:5](Br)=[CH:4][N:3]=1.[S:15]1[CH:19]=[CH:18][CH:17]=[C:16]1B(O)O>>[Cl:1][C:2]1[N:7]=[C:6]([NH:8][C@H:9]([CH2:12][CH3:13])[CH2:10][OH:11])[C:5]([C:16]2[S:15][CH:19]=[CH:18][CH:17]=2)=[CH:4][N:3]=1

Participants

3

Reactant 2

HCID 27339602-Thiopheneboronic acidHCID 58891316(R)-2-(2-chloro-5-bromopyrimidine-4-ylamino)butan-1-ol

Product 1

HCID 58985648(R)-2-(2-chloro-5-(2-thienyl)pyrimidine-4-ylamino)butan-1-olYield 71%

Procedure

In the reaction of (R)-2-(2-chloro-5-bromopyrimidine-4-ylamino)butan-1-ol (18.17 g, 64.8 mmol) with thiophen-2-boronic acid (e. g.: Aldrich, Acros, Apin) (9.12 g, 128.0 mmol) according to procedure 3, the desired product is obtained in 71% yield (13.1 g) after chromatographic purification (silica gel, ethyl acetate/hexane (20%-50% ethyl acetate)).

Sources & evidence

ORD record
ord-ce19478673f84688b18c871ad877a48d
Source dataset
uspto-grants-2010_11
Patent number
US07825128B2

Reaction notes

Loading…