6-Heptynoic acid → 7-(4,5-Diphenylpyrimidin-2-yl)-6-heptynoic Acid

HRID 2233273Notes

Reaction equation

HRID 2233273 reaction equation
[C:1]([OH:9])(=[O:8])[CH2:2][CH2:3][CH2:4][CH2:5][C:6]#[CH:7].Cl[C:11]1[N:16]=[C:15]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:14]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[CH:13][N:12]=1>C(N(CC)CC)C.[Cu]I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[C:17]1([C:15]2[C:14]([C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)=[CH:13][N:12]=[C:11]([C:7]#[C:6][CH2:5][CH2:4][CH2:3][CH2:2][C:1]([OH:9])=[O:8])[N:16]=2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 2

HCID 43779506-Heptynoic acidHCID 126742762-Chloro-4,5-diphenylpyrimidine

Product 1

HCID 177573697-(4,5-Diphenylpyrimidin-2-yl)-6-heptynoic AcidYield 3.4%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8471TriethylamineSolvent

Conditions

Temperature
50 °C

Procedure

88 mg (0.7 mmol) of 6-heptynoic acid, 6 mg (0.07 eq.) of copper(I) iodide and 14 mg (0.04 eq.) of bis(triphenylphosphine)palladium(II) chloride were added to a solution of 114 mg (0.5 mmol) of 2-chloro-4,5-diphenylpyrimidine in 5 ml of triethylamine, and the mixture was stirred at 50° C. for 1 hour. The residue after evaporation was purified by preparative HPLC (method A). 6 mg (3%) of the desired product were obtained.

Workup

  1. customThe residue after evaporation
  2. customwas purified by preparative HPLC (method A)

Sources & evidence

ORD record
ord-9650b360b9f14ad5afe6d2401338778e
Source dataset
uspto-grants-2010_05
Patent number
US07709490B2

Reaction notes

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