Sodium Carbonate → HCID 11280481, compound

HRID 2216313Notes

Reaction equation

HRID 2216313 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([NH:8][C:9]2[C:14]([CH3:15])=[CH:13][C:12]([CH3:16])=[CH:11][C:10]=2[CH3:17])[C:5]([S:18]([C:21]2[CH:26]=[CH:25][C:24](OS(C(F)(F)F)(=O)=O)=[CH:23][CH:22]=2)(=[O:20])=[O:19])=[CH:4][N:3]=1.[CH3:35]B(O)O.C([O-])([O-])=O.[Na+].[Na+].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.COCCOC>[CH3:1][C:2]1[N:7]=[C:6]([NH:8][C:9]2[C:14]([CH3:15])=[CH:13][C:12]([CH3:16])=[CH:11][C:10]=2[CH3:17])[C:5]([S:18]([C:21]2[CH:26]=[CH:25][C:24]([CH3:35])=[CH:23][CH:22]=2)(=[O:20])=[O:19])=[CH:4][N:3]=1

Participants

8

Reactant 4

HCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 139377Methylboronic AcidHCID 86595018HCID 86595018, compound

Product 1

HCID 11280481HCID 11280481, compoundYield 65.1%

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

A mixture of trifluoromethanesulfonic acid 4-[2-methyl-4-(2,4,6-trimethylphenylamino)-pyrimidine-5-sulfonyl]-phenyl ester (158 mg, 0.306 mmol), prepared by the method described in Example 22, methylboronic acid (36 mg, 0.61 mmol), 2 M Na2CO3 (2.0 mL, 4.0 mmol), and DME (4 mL) was degassed with N2 for 10 min, and then PdCl2(PPh3)2 (43 mg, 0.061 mmol) and triphenylphosphine (32 mg, 0.12 mmol) were added. The mixture was refluxed under N2 for 2 h and then cooled to room temperature. The reaction mixture was diluted with water, and extracted (3×) with EtOAc. The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by chromatography on silica gel (67:33 hexanes/EtOAc) to provide the desired product (76 mg, 65%) as a white solid: mp 202–204° C.; 1H NMR (300 MHz, CDCl3) δ 8.75 (s, 1H), 8.23 (br s, 1H), 7.84 (d, J=8.4 Hz, 2H), 7.33 (d, J=8.4 Hz, 2H), 6.91 (s, 2H), 2.43 (s, 3H), 2.38 (s, 3H), 2.30 (s, 3H), 2.00 (s, 6H); ESI MS m/z 382 [(M+H)+, calcd for C21H24N3O2S, 382.2].

Workup

  1. customprepared by the method
  2. customwas degassed with N2 for 10 min
  3. temperatureThe mixture was refluxed under N2 for 2 h
  4. extractionextracted (3×) with EtOAc
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by chromatography on silica gel (67:33 hexanes/EtOAc)

Sources & evidence

ORD record
ord-9aad94727db841ff8c8a1ebcfb1e4c99
Source dataset
uspto-grants-2006_09
Patent number
US07112585B2

Reaction notes

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