Potassium Phosphate, Tribasic → 1-(4-Cyclopropylpyridin-3-yl)-3-(2-(trifluoromethyl) pyrimidin-4-yl)imidazolidin-2-one

HRID 523539Notes

Reaction equation

HRID 523539 reaction equation
[CH:1]1([C:4]2[CH:9]=[CH:8][N:7]=[CH:6][C:5]=2[N:10]2[CH2:14][CH2:13][NH:12][C:11]2=[O:15])[CH2:3][CH2:2]1.Cl[C:17]1[CH:22]=[CH:21][N:20]=[C:19]([C:23]([F:26])([F:25])[F:24])[N:18]=1.CN[C@@H]1CCCC[C@H]1NC.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>[Cu](I)I.O1CCOCC1>[CH:1]1([C:4]2[CH:9]=[CH:8][N:7]=[CH:6][C:5]=2[N:10]2[CH2:14][CH2:13][N:12]([C:17]3[CH:22]=[CH:21][N:20]=[C:19]([C:23]([F:26])([F:25])[F:24])[N:18]=3)[C:11]2=[O:15])[CH2:3][CH2:2]1

Participants

7

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 2733821trans-N,N'-dimethyl-1,2-cyclohexanediamineHCID 152943694-Chloro-2-(trifluoromethyl)pyrimidineHCID 709820071-(4-Cyclopropylpyridin-3-yl)imidazolidin-2-one

Product 1

HCID 665765651-(4-Cyclopropylpyridin-3-yl)-3-(2-(trifluoromethyl) pyrimidin-4-yl)imidazolidin-2-oneYield 12%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 312751,4-DioxaneSolvent

Procedure

Using analogous reagents and reaction conditions as described in Example 1 above, 1-(4-cyclopropylpyridin-3-yl)imidazolidin-2-one (I-1d: 100 mg, 0.492 mmol) was reacted with 4-chloro-2-(trifluoromethyl)pyrimidine (108 mg, 0.591 mmol), 1,4-dioxane (5 mL), copper iodide (9.3 mg, 0.049 mmol), trans-N,N′-dimethylcyclohexane-1,2-diamine (6.9 mg, 0.049 mmol) and potassium phosphate (313 mg, 1.47 mmol) to afford the crude product. Purification by column chromatography on silica gel (1% methanol in CHCl3), followed by preparative HPLC afforded 20 mg of the product (12% yield).

Workup

  1. customreagents and reaction conditions
  2. customto afford the crude product
  3. customPurification by column chromatography on silica gel (1% methanol in CHCl3)

Sources & evidence

ORD record
ord-4e53ea52548143f79ba6dc3b6af211f4
Source dataset
uspto-grants-2016_05
Patent number
US09339501B2

Reaction notes

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