3-Chloro-4-[3-(trifluoromethyl)phenoxy]aniline → 5-(3-chloropropyl)-N-{3-chloro-4-[3-(trifluoromethyl)phenoxy]phenyl}-5H-pyrrolo[3,2-d]pyrimidin-4-amine

HRID 1926110Notes

Reaction equation

HRID 1926110 reaction equation
Cl[C:2]1[C:3]2[N:10]([CH2:11][CH2:12][CH2:13][Cl:14])[CH:9]=[CH:8][C:4]=2[N:5]=[CH:6][N:7]=1.[Cl:15][C:16]1[CH:17]=[C:18]([CH:20]=[CH:21][C:22]=1[O:23][C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([C:30]([F:33])([F:32])[F:31])[CH:25]=1)[NH2:19]>C(O)(C)C>[Cl:14][CH2:13][CH2:12][CH2:11][N:10]1[C:3]2[C:2]([NH:19][C:18]3[CH:20]=[CH:21][C:22]([O:23][C:24]4[CH:29]=[CH:28][CH:27]=[C:26]([C:30]([F:31])([F:32])[F:33])[CH:25]=4)=[C:16]([Cl:15])[CH:17]=3)=[N:7][CH:6]=[N:5][C:4]=2[CH:8]=[CH:9]1

Participants

4

Reactant 2

HCID 196269843-Chloro-4-[3-(trifluoromethyl)phenoxy]anilineHCID 860848304-chloro-5-(3-chloropropyl)-5H-pyrrolo[3,2-d]pyrimidine

Product 1

HCID 675204045-(3-chloropropyl)-N-{3-chloro-4-[3-(trifluoromethyl)phenoxy]phenyl}-5H-pyrrolo[3,2-d]pyrimidin-4-amineYield 88.5%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 4-chloro-5-(3-chloropropyl)-5H-pyrrolo[3,2-d]pyrimidine (789 mg), 3-chloro-4-[3-(trifluoromethyl)phenoxy]aniline (1.09 g) and isopropyl alcohol (5 mL) was stirred at 80° C. for 4.5 hrs. The mixture was concentrated under reduced pressure, saturated aqueous sodium hydrogen carbonate (30 mL) was added to the residue, and the mixture was extracted with ethyl acetate (40 mL×3). The organic layers were combined, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent, hexane:ethyl acetate=90:10→20:80) to give the title compound (1.46 g).

Workup

  1. concentrationThe mixture was concentrated under reduced pressure, saturated aqueous sodium hydrogen carbonate (30 mL)
  2. additionwas added to the residue
  3. extractionthe mixture was extracted with ethyl acetate (40 mL×3)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (eluent, hexane:ethyl acetate=90:10→20:80)

Sources & evidence

ORD record
ord-b5589bd0ec424ce3aa1adeb753e1d803
Source dataset
uspto-grants-2012_05
Patent number
US08178543B2

Reaction notes

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