Diisopropylethylamine → (2-Chloro-6-trifluoromethylpyrimidin-4-yl)-methyl-(4-trifluoromethoxyphenyl)-amine

HRID 1907836Notes

Reaction equation

HRID 1907836 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[CH:5]=[C:4]([C:9]([F:12])([F:11])[F:10])[N:3]=1.[CH3:13][NH:14][C:15]1[CH:20]=[CH:19][C:18]([O:21][C:22]([F:25])([F:24])[F:23])=[CH:17][CH:16]=1.C(N(C(C)C)CC)(C)C>C1COCC1>[Cl:1][C:2]1[N:7]=[C:6]([N:14]([CH3:13])[C:15]2[CH:20]=[CH:19][C:18]([O:21][C:22]([F:23])([F:24])[F:25])=[CH:17][CH:16]=2)[CH:5]=[C:4]([C:9]([F:12])([F:11])[F:10])[N:3]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 3342032,4-Dichloro-6-(trifluoromethyl)pyrimidineHCID 737351n-Methyl-4-(trifluoromethoxy)aniline

Product 1

HCID 57507179(2-Chloro-6-trifluoromethylpyrimidin-4-yl)-methyl-(4-trifluoromethoxyphenyl)-amineYield 56%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2,4-Dichloro-6-trifluoromethylpyrimidine (XXVII) (1.00 g, 4.6 mmol) was dissolved in dry THF (5 mL). To this solution was added N-methyl-4-trifluoromethoxyaniline (0.88 g, 4.6 mmol) and diisopropylethylamine (0.8 mL, 4.6 mmol). The resulting solution was stirred at room temperature for 18 hrs, then the volatiles were removed in vacuo and the residue was dissolved in CH2Cl2 (50 mL). The CH2Cl2 solution was washed with 2N HCl, dried over MgSO4, filtered and then concentrated in vacuo to give a brown color oil. Purification of the brown oil by chromatography (silica, hexane/EtOAc) afforded the product (XXVIII) as a yellow solid (0.95 g, 56%): 1H NMR (CDCl3) δ 7.42-7.27 (m, 4H), 6.4 (s, 1H), 3.5 (s, 3H); GC/MS m/z (relative intensity) 374 (26), 373 (45), 372 (76), 370 (100).

Workup

  1. customthe volatiles were removed in vacuo
  2. dissolutionthe residue was dissolved in CH2Cl2 (50 mL)
  3. washThe CH2Cl2 solution was washed with 2N HCl
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto give a brown color oil
  8. customPurification of the brown oil by chromatography (silica, hexane/EtOAc)

Sources & evidence

ORD record
ord-fa4df1b0d24f41f5b46f6ed40ee3fc15
Source dataset
uspto-grants-2013_12
Patent number
US08598182B2

Reaction notes

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