2-Thiopheneboronic acid → 2-(2-Chloro-5-(2-thienyl)pyrimidine-4-ylamino)ethanol

HRID 1169728Notes

Reaction equation

HRID 1169728 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([NH:8][CH2:9][CH2:10][OH:11])[C:5](I)=[CH:4][N:3]=1.[S:13]1[CH:17]=[CH:16][CH:15]=[C:14]1B(O)O>>[Cl:1][C:2]1[N:7]=[C:6]([NH:8][CH2:9][CH2:10][OH:11])[C:5]([C:14]2[S:13][CH:17]=[CH:16][CH:15]=2)=[CH:4][N:3]=1

Participants

3

Reactant 2

HCID 27339602-Thiopheneboronic acidHCID 595508722-(2-Chloro-5-iodopyrimidine-4-ylamino)ethanol

Product 1

HCID 589857042-(2-Chloro-5-(2-thienyl)pyrimidine-4-ylamino)ethanolYield 82%

Procedure

In the reaction of 2-(2-chloro-5-iodopyrimidine-4-ylamino)-ethanol (300 mg, 1.0 mmol) with thiophen-2-boronic acid (140 mg, 1.1 mmol) according to procedure 3, the desired product is obtained in 82% yield (210 mg) after chromatographic purification (silica gel, ethyl acetate/hexane (0%-100% ethyl acetate)).

Sources & evidence

ORD record
ord-ad2368b1e0b44ac08cb85e6434080041
Source dataset
uspto-grants-2010_11
Patent number
US07825128B2

Reaction notes

Loading…