Hydrochloric Acid → 4-(5-Chloro-2-methoxyanilino)-2-(3-pyridinyl)-6-trifluoromethylpyrimidine

HRID 1765274Notes

Reaction equation

HRID 1765274 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.[CH3:18][O:19][C:20]1[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][C:21]=1[NH2:22].Cl>C(O)C.O>[Cl:27][C:24]1[CH:25]=[CH:26][C:20]([O:19][CH3:18])=[C:21]([CH:23]=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:13]=[N:14][CH:15]=[CH:16][CH:17]=2)[N:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 667635-Chloro-2-methoxyanilineHCID 14859904-Chloro-2-(pyridin-3-yl)-6-(trifluoromethyl)pyrimidine

Product 1

HCID 227324694-(5-Chloro-2-methoxyanilino)-2-(3-pyridinyl)-6-trifluoromethylpyrimidineYield 68.2%

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Procedure

A mixture of 4-chloro-2-(3-pyridinyl)-6-trifluoromethylpyrimidine (100 mg, 0.385 mmol), 2-methoxy-5-chloroaniline (90 mg, 0.577 mmol) and 2N HCl (150 μl) in 1:1 ethanol/water (5 ml) was refluxed for 48 h. The resulting yellow solid was collected by filtration, washed with water, ethanol/water (1:4) and then dried under vacuum to give the title compound (100 mg, 67%). 1H NMR (CDCl3): 9.66 (d, J=1.8 Hz, 1H), 8.70–8.76 (m, 2H), 7.68 (dd, J=7.5, 1.0 Hz, 1H), 7.44 (dd, J=7.5, 1.0 Hz, 1H), 7.09 (dd, J=8.7, 2.7 Hz, 1H), 6.92 (s, 1H), 6.87 (d, J=8.7 Hz, 1H), 3.91 (s, 3H).

Workup

  1. temperaturewas refluxed for 48 h
  2. filtrationThe resulting yellow solid was collected by filtration
  3. washwashed with water, ethanol/water (1:4)
  4. customdried under vacuum

Sources & evidence

ORD record
ord-7c3f01a68ddd4c3db59e163396bc4bd6
Source dataset
uspto-grants-2007_06
Patent number
US07226927B2

Reaction notes

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