Potassium Phosphate, Tribasic → HCID 136368403, compound

HRID 2100559Notes

Reaction equation

HRID 2100559 reaction equation
Br[C:2]1[CH:22]=[N:21][C:5]2[N:6]=[C:7]([CH2:11][CH2:12][CH2:13][CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[NH:8][C:9](=[O:10])[C:4]=2[CH:3]=1.[CH:23]1(B(O)O)[CH2:25][CH2:24]1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].C1(P(C2CCCCC2)C2CCCCC2)CCCCC1>C1(C)C=CC=CC=1.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.ClCCl>[CH:23]1([C:2]2[CH:22]=[N:21][C:5]3[N:6]=[C:7]([CH2:11][CH2:12][CH2:13][CH2:14][C:15]4[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=4)[NH:8][C:9](=[O:10])[C:4]=3[CH:3]=2)[CH2:25][CH2:24]1

Participants

9

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 75806TricyclohexylphosphineHCID 2760897Cyclopropylboronic acidHCID 135899296HCID 135899296, compound

Product 1

HCID 136368403HCID 136368403, compoundYield 6%

Reagents, catalysts & solvents 4

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

Palladium(II) acetate (1 mg, 4.5 μmol) was added to a degassed suspension of 6-bromo-2-(4-phenyl-butyl)-3H-pyrido[2,3-d]pyrimidin-4-one (20 mg, 55 μmol; example 26), cyclopropyl boronic acid (10 mg, 110 μmol), potassium phosphate (59 mg, 275 μmol) and tricyclohexylphosphine (3 mg, 9 μmol) in toluene (360 μl) and water (24 μl) under an argon atmosphere. The reaction mixture was heated for 14 h to 100° C. and poured onto ice cold isopropyl acetate/brine 1/1. The layers were separated, the aqueous layer was extracted two times with isopropyl acetate, the combined extracts were washed with brine and dried over sodium sulfate. Removal of the solvent under reduced pressure left a yellow solid which was purified by preparative thin layer chromatography (silica gel, isopropyl acetate/heptane) to give 6-cyclopropyl-2-(4-phenyl-butyl)-3H-pyrido[2,3-d]pyrimidin-4-one (1 mg, 3.1 μmol; 6%) as yellow crystals. MS: m/e=320.2 [M+H+].

Workup

  1. temperatureThe reaction mixture was heated for 14 h to 100° C.
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted two times with isopropyl acetate
  4. washthe combined extracts were washed with brine
  5. dry with materialdried over sodium sulfate
  6. customRemoval of the solvent under reduced pressure
  7. waitleft a yellow solid which
  8. customwas purified by preparative thin layer chromatography (silica gel, isopropyl acetate/heptane)

Sources & evidence

ORD record
ord-6ee95202bfaa43138ac4617bc30e2f9b
Source dataset
uspto-grants-2009_08
Patent number
US07572801B2

Reaction notes

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