Triethylamine → N-(3-(2-chloro-5-((3-fluorophenyl)amino)pyrimidin-4-yl)phenyl)acrylamide

HRID 2368192Notes

Reaction equation

HRID 2368192 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:8]2[C:13]([NH:14][C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([F:21])[CH:16]=3)=[CH:12][N:11]=[C:10]([Cl:22])[N:9]=2)[CH:5]=[CH:6][CH:7]=1.[C:23](Cl)(=[O:26])[CH:24]=[CH2:25].C(N(CC)CC)C>>[Cl:22][C:10]1[N:9]=[C:8]([C:4]2[CH:3]=[C:2]([NH:1][C:23](=[O:26])[CH:24]=[CH2:25])[CH:7]=[CH:6][CH:5]=2)[C:13]([NH:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([F:21])[CH:16]=2)=[CH:12][N:11]=1

Participants

4

Reactant 3

HCID 8471TriethylamineHCID 13140Acryloyl chlorideHCID 866775204-(3-aminophenyl)-2-chloro-N-(3-fluorophenyl)pyrimidin-5-amine

Product 1

HCID 71469247N-(3-(2-chloro-5-((3-fluorophenyl)amino)pyrimidin-4-yl)phenyl)acrylamideYield 18.4%

Procedure

4-(3-Aminophenyl)-2-chloro-N-(3-fluorophenyl)pyrimidin-5-amine (15 mg, 0.048 mmol) was added to a solution of acryloyl chloride (4.24 μL, 0.052 mmol) in the presence of triethylamine (0.013 mL, 0.095 mmol) at 0° C., and the reaction mixture was stirred for 12 h at rt. The reaction was monitored by TLC. After completion of the reaction, the compound was purified by column chromatography to give the title compound (3.26 mg, 16% yield). ESI-MS: m/z 369.09 [M+H]+.

Workup

  1. customAfter completion of the reaction
  2. customthe compound was purified by column chromatography

Sources & evidence

ORD record
ord-5005b2b5c8514383b0034d13fe4cdf70
Source dataset
uspto-grants-2014_04
Patent number
US08703767B2

Reaction notes

Loading…