Diisopropylethylamine → N-(5-tert-butyl-2-methylphenyl)-2-chloro-5-fluoropyrimidin-4-amine

HRID 888996Notes

Reaction equation

HRID 888996 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[C:5]([F:9])=[CH:4][N:3]=1.[CH3:10][C:11]1[CH:17]=[CH:16][C:15]([C:18]([CH3:21])([CH3:20])[CH3:19])=[CH:14][C:12]=1[NH2:13].C(N(C(C)C)CC)(C)C>C(O)C>[C:18]([C:15]1[CH:16]=[CH:17][C:11]([CH3:10])=[C:12]([NH:13][C:6]2[C:5]([F:9])=[CH:4][N:3]=[C:2]([Cl:1])[N:7]=2)[CH:14]=1)([CH3:21])([CH3:20])[CH3:19]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 2507052,4-Dichloro-5-fluoropyrimidineHCID 130899795-tert-Butyl-2-methylaniline

Product 1

HCID 59191944N-(5-tert-butyl-2-methylphenyl)-2-chloro-5-fluoropyrimidin-4-amineYield 68.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2,4-dichloro-5-fluoropyrimidine (307 mg, 1.84 mmol), 2-methyl-5-t-butylaniline (300 mg, 1.84 mmol) and diisopropylethylamine (2 mL) in ethanol (2 mL) was heated at 80° C. for 16 h in an oil bath. The mixture was cooled to room temperature and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel Biotage 40M, eluting with EtOAc/hexane to afford the product (369 mg, 68%) as a solid.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe residue was purified by column chromatography on silica gel Biotage 40M
  3. washeluting with EtOAc/hexane

Sources & evidence

ORD record
ord-2220d4aaa3aa43c1ac090eb51e4aaf58
Source dataset
uspto-grants-2012_08
Patent number
US08252803B2

Reaction notes

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