Dimethyl Sulfoxide → 2-(4-(5-Bromopyrimidin-2-ylamino)phenyl)acetic acid

HRID 2067873Notes

Reaction equation

HRID 2067873 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[CH:4][CH:3]=1.[Br:12][C:13]1[CH:14]=[N:15][C:16](Cl)=[N:17][CH:18]=1.CC1C=CC(S(O)(=O)=O)=CC=1.CS(C)=O>O1CCOCC1>[Br:12][C:13]1[CH:14]=[N:15][C:16]([NH:1][C:2]2[CH:3]=[CH:4][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[CH:6][CH:7]=2)=[N:17][CH:18]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 6101p-Toluenesulfonic acidHCID 145334-Aminophenylacetic acidHCID 6066655-Bromo-2-chloropyrimidine

Product 1

HCID 687273072-(4-(5-Bromopyrimidin-2-ylamino)phenyl)acetic acid

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

2-(4-Aminophenyl)acetic acid (4.56 mmol), 5-bromo-2-chloropyrimidine 4 (3.26 mmol), and p-TSA (0.842 mmol) are heated at reflux in 1,4-dioxane (10 mL) and DMSO (2 mL) for 16 h. The mixture is poured onto water and extracted with EtOAc. Concentration of the organic phase gives 2-(4-(5-Bromopyrimidin-2-ylamino)phenyl)acetic acid 22 as a yellow solid. 1H NMR (400 MHz, d6-DMSO) δ 9.84 (s, 1H), 8.58 (s, 2H), 7.61 (d, J=8.4 Hz, 2H), 7.17 (d, J=8.4 Hz, 2H), 3.50 (s, 2H). MS (m/z) (M+1)+: 308.0, 310.0.

Workup

  1. additionThe mixture is poured onto water
  2. extractionextracted with EtOAc

Sources & evidence

ORD record
ord-8287f92526604cfcba9818620ddcbd0f
Source dataset
uspto-grants-2012_10
Patent number
US08293757B2

Reaction notes

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