Hydrochloric Acid → 4-(2-Methyl-5-nitroanilino)-2-(4-pyridinyl)-6-(trifluoromethyl)pyrimidine

HRID 1765232Notes

Reaction equation

HRID 1765232 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][N:15]=[CH:14][CH:13]=2)[N:3]=1.[CH3:18][C:19]1[CH:25]=[CH:24][C:23]([N+:26]([O-:28])=[O:27])=[CH:22][C:20]=1[NH2:21].Cl.[OH-].[Na+]>O.C(O)C>[CH3:18][C:19]1[CH:25]=[CH:24][C:23]([N+:26]([O-:28])=[O:27])=[CH:22][C:20]=1[NH:21][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][N:15]=[CH:14][CH:13]=2)[N:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 74442-Methyl-5-NitroanilineHCID 14798Sodium HydroxideHCID 14859894-Chloro-2-(pyridin-4-yl)-6-(trifluoromethyl)pyrimidine

Product 1

HCID 227323994-(2-Methyl-5-nitroanilino)-2-(4-pyridinyl)-6-(trifluoromethyl)pyrimidineYield 30%

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Procedure

A mixture of 4-chloro-2-(4-pyridinyl)-6-(trifluoromethyl)pyrimidine (1 g, 3.90 mmol), 2-methyl-5-nitroaniline (890 mg, 5.90 mmol), and 2N HCl (3 ml) in water:ethanol (1:1, 200 ml) was refluxed for 48 h. The mixture was cooled to room temperature and basified with aqueous 2N NaOH to pH 10–12. The mixture was extracted with ethyl acetate (200 ml), washed with water (2×100 ml), with aqueous saturated NaCl (1×100 ml) and dried over anhydrous sodium sulfate. The ethyl acetate solution was rotary evaporated to dryness to give a tan solid (377 mg, 30%). 1H NMR (CDCl3): 8.90 (s, 1H), 8.80 (dd, J=1.8, 4.8 Hz, 2H), 8.30 (dd, J=1.5, 4.5 Hz, 2H), 8.09 (dd, J 2.4, 8.1 Hz, 1H), 7.51 (d, J=8.4 Hz, 1H), 6.99 (s, 1H), 6.87 (s, 1H), 2.47 (s, 3H).

Workup

  1. temperaturewas refluxed for 48 h
  2. extractionThe mixture was extracted with ethyl acetate (200 ml)
  3. washwashed with water (2×100 ml), with aqueous saturated NaCl (1×100 ml)
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe ethyl acetate solution was rotary evaporated to dryness

Sources & evidence

ORD record
ord-3fe9844898ea4ad49541856f62da10cc
Source dataset
uspto-grants-2007_06
Patent number
US07226927B2

Reaction notes

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