Sodium Carbonate → HCID 178432674, compound

HRID 1371131Notes

Reaction equation

HRID 1371131 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.[CH3:18]B(O)O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C([O-])([O-])=O.[Na+].[Na+]>O.[Pd].[Pd].C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.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]([CH3:18])[N:7]=1

Participants

9

Reactant 4

HCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 139377Methylboronic AcidHCID 178432852HCID 178432852, compound

Product 1

HCID 178432674HCID 178432674, compoundYield 62%

Reagents, catalysts & solvents 4

HCID 9832798Tris(dibenzylideneacetone) dipalladiumCatalystHCID 702EthanolSolventHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

A mixture of 4-chloro-2-methyl-6-phenyl-pyrrolo[3,2-d]pyrimidine (Example 1(e)) (80 mg, 0.33 mmol), methylboronic acid (Aldrich Chemical Company) (49 mg, 0.82 mmol), tris(dibenzylideneacetone) dipalladium(0) (Aldrich Chemical Company) (9.4 mg, 0.0103 mmol) and triphenylphosphine (Aldrich Chemical Company) (10.8 mg, 0.042 mmol) in a mixed solvent (1000 μL of toluene, 500 μL of 1.0 M Na2CO3, and 250 μL of ethanol) was heated at reflux under N2 overnight. Upon cooling to the room temperature, the reaction mixture was diluted with H2O (20 mL) and extracted with CHCl3 (4×40 mL). The organic extracts were dried over Na2SO4, filtered, and concentrated with a rotary evaporator. This material was purified by preparative thin layer chromatography on silica gel with 1:1 THF:hexanes as eluant to afford 30 mg (62%) of the title compound as a yellow solid. 1H NMR (CDCl3; 400 MHz): δ 8.38 (s, 1), 7.74 (d, 2, J=7.0), 7.53 (t, 2, J=7.0), 7.45 (t, 1, J=7.0), 6.87 (d, 1, J=1.7), 2.79 (s, 3), 2.74 (s, 3). MS m/z: 224 (M+1), 222 (M−1).

Workup

  1. temperaturewas heated
  2. temperatureat reflux under N2 overnight
  3. extractionextracted with CHCl3 (4×40 mL)
  4. dry with materialThe organic extracts were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated with a rotary evaporator
  7. customThis material was purified by preparative thin layer chromatography on silica gel with 1:1 THF

Sources & evidence

ORD record
ord-f969a4266fdf49aaadeaa393bd25dcb1
Source dataset
uspto-grants-2003_06
Patent number
US06583154B1

Reaction notes

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