4,6-Dichloropyrimidine → HCID 57708302, compound

HRID 2093498Notes

Reaction equation

HRID 2093498 reaction equation
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[CH:4][N:3]=1.[O:9]([C:16]1[CH:17]=[C:18]([CH:20]=[CH:21][CH:22]=1)[NH2:19])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.CCN(C(C)C)C(C)C>C(O)CCC>[Cl:8][C:6]1[N:5]=[CH:4][N:3]=[C:2]([NH:19][C:18]2[CH:20]=[CH:21][CH:22]=[C:16]([O:9][C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH:17]=2)[CH:7]=1

Participants

5

Reactant 3

HCID 709434,6-DichloropyrimidineHCID 771353-PhenoxyanilineHCID 81531Diisopropylethylamine

Product 1

HCID 57708302HCID 57708302, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A solution of 4,6-dichloropyrimidine (0.5 g, 3.3 mmol), 3-phenoxyaniline (0.75 g, 4 mmol) and DIPEA (0.65 g, 5 mmol) in n-butanol (5 mL) was subjected to microwave irradiation (110° C., 30 min). The reaction mixture was cooled, concentrated under reduced pressure and the residue was dissolved in EtOAc (10 mL). This solution was washed with water (5 mL) and brine (5 mL), and was dried over Na2SO4. Concentrated under reduced pressure gave a residue that was purified by column chromatography (SiO2, 60-120, hexane/ethylacetate, 8/2) to give 6-chloro-N-(3-phenoxyphenyl)pyrimidine-4-amine (0.56 g, 56%) as an off-white solid.

Workup

  1. temperatureThe reaction mixture was cooled
  2. concentrationconcentrated under reduced pressure
  3. dissolutionthe residue was dissolved in EtOAc (10 mL)
  4. washThis solution was washed with water (5 mL) and brine (5 mL)
  5. dry with materialwas dried over Na2SO4
  6. concentrationConcentrated under reduced pressure
  7. customgave a residue that
  8. customwas purified by column chromatography (SiO2, 60-120, hexane/ethylacetate, 8/2)

Sources & evidence

ORD record
ord-641006595885412283f55346685c93fe
Source dataset
uspto-grants-2013_05
Patent number
US08445498B2

Reaction notes

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