Hydrochloric Acid → 4-(2,5-Dimethoxyanilino)-2-phenyl-6-(trifluoromethyl)pyrimidine

HRID 2084125Notes

Reaction equation

HRID 2084125 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][CH:13]=2)[N:3]=1.[CH3:18][O:19][C:20]1[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][C:21]=1[NH2:22].Cl.[OH-].[Na+]>O.C(O)C>[CH3:18][O:19][C:20]1[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][C:21]=1[NH:22][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][CH:13]=2)[N:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 76132,5-DimethoxyanilineHCID 14798Sodium HydroxideHCID 6141014-Chloro-2-phenyl-6-(trifluoromethyl)pyrimidine

Product 1

HCID 227324924-(2,5-Dimethoxyanilino)-2-phenyl-6-(trifluoromethyl)pyrimidineYield 50%

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Procedure

A mixture of 4-chloro-2-phenyl-6-(trifluoromethyl)pyrimidine (50 mg, 0.193 mmol), 2,5-dimethoxyaniline (44 mg, 0.290 mmol) and aqueous 2N HCl (150 μl) in water:ethanol (1:1, 10 ml) was refluxed for 48 h. The mixture was cooled to room temperature and then basified with aqueous 2N NaOH to pH 10-12. The resulting precipitate was filtered, washed with water, water:ethanol (2:1) and dried under vacuo to give a gray solid (36 mg, 50%). 1H NMR (CDCl3): 8.51-8.48 (m, 2H), 8.14 (s, 1H), 7.51-7.48 (m, 4H), 6.89 (s, 1H), 6.88 (d, J=9.3 Hz, 1H), 6.66 (dd, J=3.0, 8.7 Hz, 1H), 3.90 (s, 3H), 3.87 (s, 3H).

Workup

  1. temperaturewas refluxed for 48 h
  2. filtrationThe resulting precipitate was filtered
  3. washwashed with water, water:ethanol (2:1)
  4. customdried under vacuo

Sources & evidence

ORD record
ord-b9439d31be2841aea55e0032d2b80f14
Source dataset
uspto-grants-2004_04
Patent number
US06716851B2

Reaction notes

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