Sodium Carbonate → HCID 178432532, compound

HRID 1371134Notes

Reaction equation

HRID 1371134 reaction equation
Cl[C:2]1[N:7]=[C:6]([CH3:8])[NH:5][C:4]2=[CH:9][C:10]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[N:11][C:3]=12.[N:18]1[CH:23]=[CH:22][CH:21]=[C:20](B(O)O)[CH:19]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C([O-])([O-])=O.[Na+].[Na+]>O.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].C(O)C.C1(C)C=CC=CC=1>[CH3:8][C:6]1[NH:5][C:4]2=[CH:9][C:10]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[N:11][C:3]2=[C:2]([C:20]2[CH:19]=[N:18][CH:23]=[CH:22][CH:21]=2)[N:7]=1

Participants

9

Reactant 4

HCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 27343783-Pyridinylboronic acidHCID 178432852HCID 178432852, compound

Product 1

HCID 178432532HCID 178432532, compoundYield 64%

Reagents, catalysts & solvents 4

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 702EthanolSolventHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

A mixture of 4-chloro-2-methyl-6-phenylpyrrolo[3,2-d]pyrimidine (Example 1(e)) (230 mg, 0.94 mmol), 3-pyridinylboronic acid (Frontier Scientific) (139 mg, 1.13 mmol), tris(dibenzylideneacetone)dipalladium(0) (Aldrich Chemical Company) (22 mg, 0.024 mmol) and triphenylphosphine (Aldrich Chemical Company) (49 mg, 0.19 mmol) in a mixture of solvents (1.2 mL of toluene, 0.3 mL of 1.0 M Na2CO3 and 0.3 mL of ethanol) was heated at reflux under N2 for 40 h. Upon cooling to the room temperature, the reaction mixture was diluted with H2O (20 mL), and the crude product was extracted with CHCl3 (3×40 mL). The organic extracts were washed with H2O (50 mL), saturated NaCl (50 mL), dried over Na2SO4 and concentrated with a rotary evaporator. Chromatography on silica gel with a gradient eluant of MeOH (0-4%):CH2Cl2 (100-96%) afforded 171 mg (64%) of the title compound as a yellow solid. Mp: 252-254 C. 1H NMR (CDCl3; 400 MHz): δ 2.89 (s, 3), 6.99 (s, 1), 7.46 (m, 4), 7.78 (d, 2, J=7.1), 8.37 (d, 1, J=7.7), 8.66 (d, 1, J=3.9), 9.31 (s, 1), 9.50 (s, 1). MS m/z: 287 (M+1), 285 (M−1). HRMS: Calcd for M+H: 287.1297. Found: 287.1288.

Workup

  1. temperaturewas heated
  2. temperatureat reflux under N2 for 40 h
  3. extractionthe crude product was extracted with CHCl3 (3×40 mL)
  4. washThe organic extracts were washed with H2O (50 mL), saturated NaCl (50 mL)
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated with a rotary evaporator

Sources & evidence

ORD record
ord-c0d6c4a0b99e48729bca9dd4ea2a0c67
Source dataset
uspto-grants-2003_06
Patent number
US06583154B1

Reaction notes

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