Thiophenol → (s)-5-[2-(1-Phenylethylamino)pyrimidin-4-yl]-3-(phenylsulfanyl)-6-(3-trifluoromethylphenyl)pyridazine

HRID 394483Notes

Reaction equation

HRID 394483 reaction equation
Cl[C:2]1[N:7]=[N:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:17])([F:16])[F:15])[CH:9]=2)=[C:4]([C:18]2[CH:23]=[CH:22][N:21]=[C:20]([NH:24][C@H:25]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[CH3:26])[N:19]=2)[CH:3]=1.[C:33]1([SH:39])[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.C(N(C(C)C)CC)(C)C>C(OCC)(=O)C>[C:27]1([C@@H:25]([NH:24][C:20]2[N:19]=[C:18]([C:4]3[CH:3]=[C:2]([S:39][C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=4)[N:7]=[N:6][C:5]=3[C:8]3[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:17])([F:16])[F:15])[CH:9]=3)[CH:23]=[CH:22][N:21]=2)[CH3:26])[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

5

Reactant 3

HCID 7969ThiophenolHCID 81531DiisopropylethylamineHCID 12070269(s)-6-Chloro-4-[2-(1-phenylethylamino)pyrimidin-4-yl]-3-(3-trifluoromethyl-phenyl)pyridazine

Product 1

HCID 10186704(s)-5-[2-(1-Phenylethylamino)pyrimidin-4-yl]-3-(phenylsulfanyl)-6-(3-trifluoromethylphenyl)pyridazineYield 51%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

Compound 10 (100 mg, 0.220 mmol), thiophenol (˜200 μL), and diisopropylethylamine (100 mL) were combined under Ar and heated at 120° C. for 3 h. The mixture was purified by flash column chromatography (hexane:ethyl acetate 70:30) to afford a foam. Crystallization from hexane:ethyl acetate afforded 59 mg (0.112 mmol, 51%) of Compound 86.

Workup

  1. customThe mixture was purified by flash column chromatography (hexane:ethyl acetate 70:30)
  2. customto afford a foam
  3. customCrystallization from hexane

Sources & evidence

ORD record
ord-cbfb592bfe56437192e746d0dd6e2de4
Source dataset
uspto-grants-2003_08
Patent number
US06602872B1

Reaction notes

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