Cesium carbonate → HCID 86345164, compound

HRID 59162Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:7]=[CH:8][C:9]=1[N:10]1[CH:14]=[C:13]([CH3:15])[N:12]=[CH:11]1)[NH2:6].Cl[C:17]1[N:22]=[C:21]([NH:23][CH:24]2[CH2:26][CH2:25]2)[CH:20]=[C:19]([CH2:27][O:28][CH2:29][C:30]([F:33])([F:32])[F:31])[N:18]=1.C(=O)([O-])[O-].[Cs+].[Cs+].C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2)CCCCC1>O1CCOCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH:24]1([NH:23][C:21]2[CH:20]=[C:19]([CH2:27][O:28][CH2:29][C:30]([F:32])([F:33])[F:31])[N:18]=[C:17]([NH:6][C:5]3[CH:7]=[CH:8][C:9]([N:10]4[CH:14]=[C:13]([CH3:15])[N:12]=[CH:11]4)=[C:3]([O:2][CH3:1])[CH:4]=3)[N:22]=2)[CH2:26][CH2:25]1

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of 3-methoxy-4-(4-methyl-1H-imidazol-1-yl)aniline (91 mg, 0.45 mmol), 2-chloro-N-cyclopropyl-6-((2,2,2-trifluoroethoxy)methyl)pyrimidin-4-amine (63 mg, 0.22 mmol), cesium carbonate (146 mg, 0.45 mmol), palladium(II) acetate (8 mg, 0.03 mmol) and 2-(dicyclohexyl-phosphino)biphenyl (12 mg, 0.03 mmol) in dioxane (1.5 mL) was heated at 120° C. in a microwave reactor for 90 minutes. The mixture was filtered through diatomeous earth, the filter pad was eluted with methanol. The eluate was concentrated in vacuum and the residue purified by preparative chromatography to give the title compound as a solid, 45 mg (45%).

Workup

filtrationThe mixture was filtered through diatomeous earth
washthe filter pad was eluted with methanol
concentrationThe eluate was concentrated in vacuum
customthe residue purified by preparative chromatography

Sources & evidence

ORD record: ord-7d3c9f90867c4da7a31ea4b49de5134a
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09439904B2

Reaction notes

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