Acetic Acid → 1-(2-((3-Bromo-5-methylphenyl)amino)pyrimidin-4-yl)ethanol

HRID 595164Notes

Reaction equation

HRID 595164 reaction equation
Cl[C:2]1[N:7]=[C:6]([CH:8]([OH:10])[CH3:9])[CH:5]=[CH:4][N:3]=1.[Br:11][C:12]1[CH:13]=[C:14]([CH:16]=[C:17]([CH3:19])[CH:18]=1)[NH2:15].C(O)(=O)C>O1CCOCC1.ClCCl>[Br:11][C:12]1[CH:13]=[C:14]([NH:15][C:2]2[N:7]=[C:6]([CH:8]([OH:10])[CH3:9])[CH:5]=[CH:4][N:3]=2)[CH:16]=[C:17]([CH3:19])[CH:18]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 30185263-Bromo-5-methylanilineHCID 772310661-(2-Chloropyrimidin-4-yl)ethanol

Product 1

HCID 1182087631-(2-((3-Bromo-5-methylphenyl)amino)pyrimidin-4-yl)ethanol

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

1-(2-Chloropyrimidin-4-yl)ethanol (5.25 g, 33.1 mmol) and 3-bromo-5-methylaniline (9.24 g, 49.7 mmol) were suspended in 1,4-dioxane (30 mL). Acetic acid (1.90 ml, 33.1 mmol) was added, and the resultant mixture was heated to 100° C. for 14 h. The reaction mixture was allowed to cool to room temperature and then was diluted with dichloromethane. The resultant solution was adsorbed on silica gel and purified by column chromatography on silica (10-100% ethyl acetate/hexanes) to afford 1-(2-((3-bromo-5-methylphenyl)amino)pyrimidin-4-yl)ethanol as a black semi-solid. MS ESI calc'd. for C13H15BrN3O [M+H]+ 308, 310. found 308, 310.

Workup

  1. custompurified by column chromatography on silica (10-100% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-7fef91b3bc604fe5aa3fab21dcc072f2
Source dataset
uspto-grants-2016_01
Patent number
US09242984B2

Reaction notes

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