Sodium Carbonate → HCID 86672858, compound

HRID 1397042Notes

Reaction equation

[Cl:1][C:2]1[N:7]=[C:6]([C:8]([O:10][CH3:11])=[O:9])[CH:5]=[C:4](Cl)[N:3]=1.[F:13][C:14]([F:26])([F:25])[O:15][C:16]1[CH:17]=[C:18](B(O)O)[CH:19]=[CH:20][CH:21]=1.C([O-])([O-])=O.[Na+].[Na+]>C1COCC1>[Cl:1][C:2]1[N:7]=[C:6]([C:8]([O:10][CH3:11])=[O:9])[CH:5]=[C:4]([C:18]2[CH:19]=[CH:20][CH:21]=[C:16]([O:15][C:14]([F:13])([F:25])[F:26])[CH:17]=2)[N:3]=1

Participants

Conditions

Temperature: 85 °C

Procedure

A 2-dram round-bottom vial was charged with methyl 2,6-dichloropyrimidine-4-carboxylate (100 mg, 0.483 mmol) and (3-(trifluoromethoxy)phenyl)boronic acid (80 mg, 0.386 mmol, 0.8 equiv) were added in THF (2 mL). Then 2M Na2CO3 (0.362 mL, 0.725 mmol, 1.5 equiv) and Pd(tetrakis)Ph3P (27.9 mg, 0.024 mmol, 0.05 equiv) were added and shaken at 85° C. overnight. The solvent was removed in the Genevac and the residue was washed with saturated NaHCO3 (1 mL). The aqueous layer was extracted with EtOAc (3×1 mL). The combined organic layers were dried on the Genevac and the crude was purified using flash purification with a gradient of 5-40% EtOAc in hexane to provide methyl 2-chloro-6-(3-(trifluoromethoxy)phenyl)pyrimidine-4-carboxylate.

Workup

customThe solvent was removed in the Genevac
washthe residue was washed with saturated NaHCO3 (1 mL)
extractionThe aqueous layer was extracted with EtOAc (3×1 mL)
customThe combined organic layers were dried on the Genevac
customthe crude was purified
customflash purification with a gradient of 5-40% EtOAc in hexane

Sources & evidence

ORD record: ord-68fc9279759d44d9b7d4b66c65302a03
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08901145B2

Reaction notes

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