Potassium Phosphate, Tribasic → HCID 86712921, compound

HRID 1424074Notes

Reaction equation

HRID 1424074 reaction equation
[Si:1]([O:8][CH2:9][C@:10]1([CH3:38])[S:16][CH2:15][CH2:14][N:13]2[C:17]([C:20]3([C:23]4[CH:28]=[CH:27][C:26](B5OC(C)(C)C(C)(C)O5)=[CH:25][CH:24]=4)[CH2:22][CH2:21]3)=[N:18][N:19]=[C:12]2[CH2:11]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].Cl[C:40]1[N:45]=[CH:44][C:43]([CH3:46])=[CH:42][N:41]=1.C1(P(C2CCCCC2)C2CCCCC2)CCCCC1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.O.C(Cl)Cl.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]>[Si:1]([O:8][CH2:9][C@:10]1([CH3:38])[S:16][CH2:15][CH2:14][N:13]2[C:17]([C:20]3([C:23]4[CH:28]=[CH:27][C:26]([C:40]5[N:45]=[CH:44][C:43]([CH3:46])=[CH:42][N:41]=5)=[CH:25][CH:24]=4)[CH2:22][CH2:21]3)=[N:18][N:19]=[C:12]2[CH2:11]1)([C:4]([CH3:5])([CH3:7])[CH3:6])([CH3:2])[CH3:3]

Participants

9

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 75806TricyclohexylphosphineHCID 5817192-Chloro-5-methylpyrimidineHCID 86712922HCID 86712922, compound

Product 1

HCID 86712921HCID 86712921, compoundYield 62%

Reagents, catalysts & solvents 4

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
140 °C

Procedure

The compound (600 mg, 1.08 mmol) obtained in Example 52-2), 2-chloro-5-methylpyrimidine (155 mg, 1.19 mmol), tris(dibenzylideneacetone)dipalladium (50 mg, 0.05 mmol), tricyclohexylphosphine (36 mg, 0.13 mmol), and tripotassium phosphate (400 mg, 1.84 mmol) were dissolved in a mixed solvent of 1,4-dioxane (3 mL) and water (1.5 mL), and the mixture was stirred at 140° C. for 2 h under microwave irradiation. The reaction mixture was cooled to room temperature, then diluted with methylene chloride (100 mL), and separated into organic and aqueous layers by the addition of saturated aqueous sodium hydrogencarbonate (30 mL). The organic layer was washed with saturated sodium chloride solution and then dried with anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the obtained residue was purified by silica gel column chromatography (elution solvent: methanol/ethyl acetate=0% to 20%) to obtain the title compound (348 mg, 62%) in a light yellow solid form.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customseparated into organic and aqueous layers
  3. additionby the addition of saturated aqueous sodium hydrogencarbonate (30 mL)
  4. washThe organic layer was washed with saturated sodium chloride solution
  5. dry with materialdried with anhydrous magnesium sulfate
  6. distillationThe solvent was distilled off under reduced pressure
  7. customthe obtained residue was purified by silica gel column chromatography (elution solvent: methanol/ethyl acetate=0% to 20%)

Sources & evidence

ORD record
ord-c96087725ecf48cbb8ca75225ba14df7
Source dataset
uspto-grants-2015_01
Patent number
US08927536B2

Reaction notes

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