Potassium Carbonate → 7-(4-chlorophenyl)-8-phenyl-2-((6-(trifluoromethyl)pyridin-3-yl)methyl)-[1,2,4]triazolo[4,3-c]pyrimidin-3(2H)-one

HRID 271399Notes

Reaction equation

HRID 271399 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13]=[CH:12][N:11]3[C:14](=[O:17])[NH:15][N:16]=[C:10]3[C:9]=2[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:4][CH:3]=1.ClC1C=CC(C2N=CN=C(NNC(OC(Cl)(Cl)Cl)=O)C=2C2C=CC=CC=2)=CC=1.Cl[CH2:53][C:54]1[CH:55]=[CH:56][C:57]([C:60]([F:63])([F:62])[F:61])=[N:58][CH:59]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:13]=[CH:12][N:11]3[C:14](=[O:17])[N:15]([CH2:53][C:54]4[CH:59]=[N:58][C:57]([C:60]([F:63])([F:61])[F:62])=[CH:56][CH:55]=4)[N:16]=[C:10]3[C:9]=2[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 27738105-(Chloromethyl)-2-(trifluoromethyl)pyridineHCID 58772821Trichloromethyl 2-(6-(4-chlorophenyl)-5-phenylpyrimidin-4-yl)hydrazinecarboxylateHCID 587728227-(4-chlorophenyl)-8-phenyl-[1,2,4]triazolo[4,3-c]pyrimidin-3(2H)-one

Product 1

HCID 119832227-(4-chlorophenyl)-8-phenyl-2-((6-(trifluoromethyl)pyridin-3-yl)methyl)-[1,2,4]triazolo[4,3-c]pyrimidin-3(2H)-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a stirred solution of 7-(4-chlorophenyl)-8-phenyl-[1,2,4]triazolo[4,3-c]pyrimidin-3(2H)-one and/or trichloromethyl 2-(6-(4-chlorophenyl)-5-phenylpyrimidin-4-yl)hydrazinecarboxylate (32.2 mg, 0.10 mmol) in DMF (2 mL) at room temperature under argon was added 5-(chloromethyl)-2-(trifluoromethyl)pyridine (29.4 mg, 0.15 mmol), followed by K2CO3 (27.6 mg, 0.20 mmol). The resulting mixture was heated at 60° C. for 1 h. The crude product was purified by silica gel column chromatography eluted with ethyl acetate-hexanes, then lyophilized from 1,4-dioxane, to obtain the title compound (18.3 mg) as an off-white lyophilate. HPLC/MS: retention time=3.90 min, [M+H]30 =482. 1H NMR (CDCl3): δ 8.80 (d, J=1.5 Hz, 1H), 8.70 (s, 1H), 7.94 (dd, J=7.9, 1.5 Hz, 1H), 7.69 (d, J=7.9 Hz, 2H), 7.28-7.47 (m, 7H), 7.20 (d, J=7.2 Hz, 2H), 5.22 (s, 2H). N-alkylation, rather than O-alkylation, was demonstrated by the presence of a 13C NMR resonance at 46.8 ppm.

Workup

  1. customThe crude product was purified by silica gel column chromatography
  2. washeluted with ethyl acetate-hexanes

Sources & evidence

ORD record
ord-87db9056024440dbb8f0dd6ef7acd320
Source dataset
uspto-grants-2008_11
Patent number
US07452892B2

Reaction notes

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