2-Thiopheneboronic acid → N-[2-(2-chloro-5-(2-thienyl)pyrimidine-4-ylamino)ethyl]acetamide

HRID 1169730Notes

Reaction equation

HRID 1169730 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([NH:8][CH2:9][CH2:10][NH:11][C:12](=[O:14])[CH3:13])[C:5](I)=[CH:4][N:3]=1.[S:16]1[CH:20]=[CH:19][CH:18]=[C:17]1B(O)O>>[Cl:1][C:2]1[N:7]=[C:6]([NH:8][CH2:9][CH2:10][NH:11][C:12](=[O:14])[CH3:13])[C:5]([C:17]2[S:16][CH:20]=[CH:19][CH:18]=2)=[CH:4][N:3]=1

Participants

3

Reactant 2

HCID 27339602-Thiopheneboronic acidHCID 59550867N-[2-(2-chloro-5-iodopyrimidine-4-ylamino)ethyl]acetamide

Product 1

HCID 58985576N-[2-(2-chloro-5-(2-thienyl)pyrimidine-4-ylamino)ethyl]acetamideYield 79%

Procedure

In the reaction of N-[2-(2-chloro-5-iodopyrimidine-4-ylamino)ethyl]-acetamide (870 mg, 2.6 mmol) with thiophen-2-boronic acid (359 mg, 2.8 mmol) according to procedure 3, the desired product is obtained in 79% yield (602 mg) after chromatographic purification (silica gel, ethyl acetate/hexane (0%-90% ethyl acetate)).

Sources & evidence

ORD record
ord-29605186a2a8437da7a89550d431531b
Source dataset
uspto-grants-2010_11
Patent number
US07825128B2

Reaction notes

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