Potassium Phosphate, Tribasic → HCID 70097755, compound

HRID 2368222Notes

Reaction equation

HRID 2368222 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:10](Br)=[CH:9][N:8]=[C:7]([CH3:12])[N:6]=1)=[O:4].[NH2:13][C:14]1[CH:15]=[N:16][CH:17]=[N:18][CH:19]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].C1(P(C2C=CC=CC=2)C2C3OC4C(=CC=CC=4P(C4C=CC=CC=4)C4C=CC=CC=4)C(C)(C)C=3C=CC=2)C=CC=CC=1>C1(C)C=CC=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.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C(Cl)(Cl)Cl.[Pd].[Pd].CCCCCCC.C(OCC)(=O)C.C(OCC)(=O)C>[CH3:1][O:2][C:3]([C:5]1[C:10]([NH:13][C:14]2[CH:15]=[N:16][CH:17]=[N:18][CH:19]=2)=[CH:9][N:8]=[C:7]([CH3:12])[N:6]=1)=[O:4]

Participants

9

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 344373Pyrimidin-5-amineHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 44631874Methyl 5-bromo-2-methylpyrimidine-4-carboxylate

Product 1

HCID 70097755HCID 70097755, compound

Reagents, catalysts & solvents 4

HCID 11029508Palladium, tris[mu-[(1,2-eta:4,5-eta)-(1E,4E)-1,5-diphenyl-1,4-pentadien-3-one]]di-, compd. with trichloromethane (1:1)CatalystHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolventHCID 21899848Ethylacetate heptaneSolvent

Conditions

Temperature
120 °C

Procedure

A suspension of 5-bromo-2-methylpyrimidine-4-carboxylic acid methyl ester (89.1 mg, 386 μmol), 5-aminopyrimidine (55.0 mg, 578 μmo) and potassium phosphate tribasic (115 mg, 540 μmol) in toluene (3 mL) was evacuated and flushed with argon. 4,5-Bis(diphenylphosphino)-9,9-dimethylxanthene (Xantphos; 73.6 mg, 127 μmol) and tris(dibenzylideneacetone)-dipalladium(0) chloroform adduct (39.9 mg, 38.6 μmol) were added and the reaction mixture was stirred at 120° C. for 16 h. The reaction mixture was poured into ethyl acetate (50 mL) and extracted with water. The organic phase was washed brine and the aqueous layers were back-extracted with ethyl acetate. The organic layers were dried and the solvent was removed. The product was obtained after silica gel chromatography using a heptane/ethyl acetate gradient as light yellow solid (55 mg, 58%).

Workup

  1. customwas evacuated
  2. customflushed with argon
  3. extractionextracted with water
  4. washThe organic phase was washed brine
  5. extractionthe aqueous layers were back-extracted with ethyl acetate
  6. customThe organic layers were dried
  7. customthe solvent was removed
  8. customThe product was obtained after silica gel chromatography

Sources & evidence

ORD record
ord-015ecd1ba5544b96b644133177d6b5e6
Source dataset
uspto-grants-2014_04
Patent number
US08703768B2

Reaction notes

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