Aniline → HCID 59598615, compound

HRID 38351Notes

Reaction equation

HRID 38351 reaction equation
Cl[C:2]1[C:7]([O:8][C:9]2[CH:14]=[C:13]([CH3:15])[C:12]([O:16][CH3:17])=[CH:11][C:10]=2[CH:18]([CH3:20])[CH3:19])=[CH:6][N:5]=[C:4]([NH2:21])[N:3]=1.C(Cl)Cl.[NH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>>[CH:18]([C:10]1[CH:11]=[C:12]([O:16][CH3:17])[C:13]([CH3:15])=[CH:14][C:9]=1[O:8][C:7]1[C:2]([NH:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[N:3][C:4]([NH2:21])=[N:5][CH:6]=1)([CH3:20])[CH3:19]

Participants

4

Reactant 3

HCID 6115AnilineHCID 6344DichloromethaneHCID 59598569HCID 59598569, compound

Product 1

HCID 59598615HCID 59598615, compound

Conditions

Temperature
100 °C

Procedure

A suspension of 4-chloro-5-(2-isopropyl-4-methoxy-5-methyl-phenoxy)-pyrimidin-2-ylamine (0.043 g, 0.14 mmol) in aniline (4 ml) was placed in a sealed tube and heated at 100° C. over night. Methylene chloride was added and insoluble solid was removed by filtration through celite. The combined methylene chloride filtrate was washed with water and dried over anhydrous sodium sulfate. After removal of the drying agent, the organic phase was concentrated under reduced pressure. The residue was purified with silica gel chromatography (2% methanol in methylene chloride) to yield a yellow oily residue, which was further purified with preparative TLC and HPLC (5 to 100% acetonitrile in water with 0.1% trifluoroacetic acid to yield 5-(2-Isopropyl-4-methoxy-5-methyl-phenoxy)-N4-phenyl-pyrimidine-2,4-diamine, M+H: 365.

Workup

  1. customwas placed in a sealed tube
  2. custominsoluble solid was removed by filtration through celite
  3. washThe combined methylene chloride filtrate was washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. customAfter removal of the drying agent
  6. concentrationthe organic phase was concentrated under reduced pressure
  7. customThe residue was purified with silica gel chromatography (2% methanol in methylene chloride)
  8. customto yield a yellow oily residue, which
  9. customwas further purified with preparative TLC and HPLC (5 to 100% acetonitrile in water with 0.1% trifluoroacetic acid

Sources & evidence

ORD record
ord-6f0cb877ee034c6c94fd6695403659c9
Source dataset
uspto-grants-2013_09
Patent number
US08524725B2

Reaction notes

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