Potassium Phosphate, Tribasic → HCID 818966, compound

HRID 2283699Notes

Reaction equation

HRID 2283699 reaction equation
C1(P(C2CCCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCCC1.[S:35]1[CH:39]=[CH:38][C:37](B(O)O)=[CH:36]1.Cl[C:44]1[N:49]=[CH:48][CH:47]=[CH:46][N:45]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>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)(CC)(C)C>[S:35]1[CH:39]=[CH:38][C:37]([C:44]2[N:49]=[CH:48][CH:47]=[CH:46][N:45]=2)=[CH:36]1

Participants

7

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 744042-ChloropyrimidineHCID 581760Thiophene-3-boronic acidHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl

Product 1

HCID 818966HCID 818966, compound

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 64052-Methyl-2-butanolSolvent

Conditions

Temperature
100 °C

Procedure

Tert-amyl alcohol (100 mL) was added to tris(dibenzylideneacetone)dipalladium(0) (460 mg), 2-(dicyclohexylphosphino)-2′,4′,6′-triisopropyl-1,1′-biphenyl (960 mg), 3-thiophene boronic acid (9.60 g), 2-chloropyrimidine (5.72 g), potassium phosphate (21.2 g), and molecular sieve 4 A (12.5 g). The reaction solution was stirred at 100° C. overnight. The insolubles were filtrated, and then the solvent was evaporated under vacuum. The resultant residue was purified by column chromatography on silica gel (developing solvent:hexane/ethyl acetate) to obtain 2-(thiophen-3-yl) pyrimidine as a white solid.

Workup

  1. filtrationThe insolubles were filtrated
  2. customthe solvent was evaporated under vacuum
  3. customThe resultant residue was purified by column chromatography on silica gel (developing solvent:hexane/ethyl acetate)

Sources & evidence

ORD record
ord-c22153ff99eb448ab4123cf48fb0d797
Source dataset
uspto-grants-2015_09
Patent number
US09145414B2

Reaction notes

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