Hydrochloric Acid → HCID 22732441, compound

HRID 1765205Notes

Reaction equation

HRID 1765205 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:13]=[N:14][CH:15]=[CH:16][CH:17]=2)[N:3]=1.[CH2:18]([O:20][C:21]1[CH:27]=[CH:26][C:25]([O:28][CH2:29][CH3:30])=[CH:24][C:22]=1[NH2:23])[CH3:19].Cl.[OH-].[Na+]>O.C(O)C>[CH2:18]([O:20][C:21]1[CH:27]=[CH:26][C:25]([O:28][CH2:29][CH3:30])=[CH:24][C:22]=1[NH:23][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[N:5]=[C:4]([C:12]2[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=2)[N:3]=1)[CH3:19]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 66756Benzenamine, 2,5-diethoxy-HCID 14859904-Chloro-2-(pyridin-3-yl)-6-(trifluoromethyl)pyrimidine

Product 1

HCID 22732441HCID 22732441, compoundYield 18%

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Procedure

A mixture of 4-chloro-2-(3-pyridinyl)-6-(trifluoromethyl)pyrimidine (50 mg, 0.193 mmol), 2,5-diethoxyaniline (52 mg, 0.290 mmol) and 2N HCl (150 μl) in water:ethanol (3:1, 10 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 and isolated as a yellow solid (14 mg, 18%). 1H NMR (CDCl3): 9.67 (s, 1H), 8.74–8.71 (m, 2H), 7.93 (s, 1H), 7.64 (s, 1H), 7.43–7.39 (m, 1H), 6.91 (s, 1H), 6.86 (d, J=9.3 Hz, 1H), 6.65 (dd, J=2.7, 8.7 Hz, 1H), 4.13–4.04 (m, 4H), 1.47–1.42 (m, 6H).

Workup

  1. temperaturewas refluxed for 24 h
  2. filtrationThe resulting precipitate was filtered

Sources & evidence

ORD record
ord-013a08a54ca046668b1ec570ee3a21dd
Source dataset
uspto-grants-2007_06
Patent number
US07226927B2

Reaction notes

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