Hydrochloric Acid → 4-(3-Ethoxyanilino)-2-(2-pyridinyl)-6-(trifluoromethyl)pyrimidine

HRID 1765195Notes

Reaction equation

HRID 1765195 reaction equation
Cl[C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[N:5]=[C:4]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=2)[N:3]=1.[CH3:18][CH2:19][O:20][C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([NH2:27])[CH:22]=1.Cl.[OH-].[Na+]>O.C(O)C>[CH2:19]([O:20][C:21]1[CH:22]=[C:23]([CH:24]=[CH:25][CH:26]=1)[NH:27][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[N:5]=[C:4]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=2)[N:3]=1)[CH3:18]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 121203-EthoxyanilineHCID 14798Sodium HydroxideHCID 113115004-Chloro-2-(2-pyridinyl)-6-(trifluoromethyl)pyrimidine

Product 1

HCID 227324714-(3-Ethoxyanilino)-2-(2-pyridinyl)-6-(trifluoromethyl)pyrimidineYield 63.6%

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Procedure

A mixture of 4-chloro-2-(2-pyridinyl)-6-(trifluoromethyl)pyrimidine (25 mg, 0.096 mmol), m-phenetidine (19 μl, 0.144 mmol), and 2N HCl (75 μl) in water:ethanol (2:1, 5 ml) was refluxed for 24 h. The mixture was cooled to room temperature and basified with aqueous 2N NaOH to pH 10–12. The resulting precipitate was filtered, washed with water, water:ethanol (2:1) and dried to give a yellow solid (22 mg, 63%). 1H NMR (CDCl3): 8.88–8.85 (m, 1H), 8.58 (d, J=8.1 Hz, 1H), 7.93–7.88 (m, 1H), 7.61 (s, 1H), 7.48–7.44 (m, 1H), 7.35 (t, J=8.4 Hz, 1H), 7.05 (s, 1H), 6.89–6.81 (m, 3H), 4.07 (q, J=7.1 Hz, 2H), 1.45 (t, J=7.1 Hz, 3H).

Workup

  1. temperaturewas refluxed for 24 h
  2. filtrationThe resulting precipitate was filtered
  3. washwashed with water, water:ethanol (2:1)
  4. customdried

Sources & evidence

ORD record
ord-ee3b77363299406cbe083d1b56aa0058
Source dataset
uspto-grants-2007_06
Patent number
US07226927B2

Reaction notes

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