Cesium carbonate → 1-(6-Chloro-2-(trifluoromethyl) pyrimidin-4-yl)-3-(4-cyclopropylpyridin-3-yl) imidazolidin-2-one

HRID 523609Notes

Reaction equation

HRID 523609 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:16][C:17]1[CH:22]=[C:21](Cl)[N:20]=[C:19]([C:24]([F:27])([F:26])[F:25])[N:18]=1.CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.C(=O)([O-])[O-].[Cs+].[Cs+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O1CCOCC1>[Cl:16][C:17]1[N:18]=[C:19]([C:24]([F:27])([F:26])[F:25])[N:20]=[C:21]([N:12]2[CH2:13][CH2:14][N:10]([C:5]3[CH:6]=[N:7][CH:8]=[CH:9][C:4]=3[CH:1]3[CH2:3][CH2:2]3)[C:11]2=[O:15])[CH:22]=1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 157131974,6-Dichloro-2-trifluoromethylpyrimidineHCID 709820071-(4-Cyclopropylpyridin-3-yl)imidazolidin-2-one

Product 1

HCID 665768931-(6-Chloro-2-(trifluoromethyl) pyrimidin-4-yl)-3-(4-cyclopropylpyridin-3-yl) imidazolidin-2-oneYield 13.24%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

Using analogous reagents and reaction conditions as described in Example 11 above, 1-(4-cyclopropylpyridin-3-yl)imidazolidin-2-one (I-1d: 100 mg, 0.492 mmol) was reacted with 4,6-dichloro-2-trifluoromethylpyrimidine (120 mg, 0.541 mmol), xantphos (25 mg, 0.04428 mmol), Pd2(dba)3 (15 mg, 0.01476 mmol), cesium carbonate (225 mg, 0.6888 mmol) and 1,4-dioxane (5 mL) in a sealed tube for 5 hours. Purification by column chromatography on silica gel (1% methanol in chloroform) followed by preparative HPLC afforded 25 mg of the product (13.24% yield).

Workup

  1. customreagents and reaction conditions
  2. customPurification by column chromatography on silica gel (1% methanol in chloroform)

Sources & evidence

ORD record
ord-46c9452e0ce647d38a6ac6259d79a29d
Source dataset
uspto-grants-2016_05
Patent number
US09339501B2

Reaction notes

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