Triphenylphosphine → HCID 86643670, compound

HRID 215855Notes

Reaction equation

HRID 215855 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(OC(=O)O[C@H:25]1[CH2:29][C@@H:28]([N:30]2[CH:38]=[N:37][C:36]3[C:31]2=[N:32][C:33]([Cl:40])=[N:34][C:35]=3[Cl:39])[CH:27]=[CH:26]1)C.[CH2:42]([C:44]1[CH:48]=[N:47][NH:46][N:45]=1)[CH3:43]>C1COCC1.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]>[Cl:40][C:33]1[N:32]=[C:31]2[C:36]([N:37]=[CH:38][N:30]2[C@@H:28]2[CH2:29][C@H:25]([N:47]3[CH:48]=[C:44]([CH2:42][CH3:43])[N:45]=[N:46]3)[CH:26]=[CH:27]2)=[C:35]([Cl:39])[N:34]=1

Participants

6

Reactant 3

HCID 11776TriphenylphosphineHCID 147949874-ethyl-2H-1,2,3-TriazoleHCID 58025019Carbonic acid (1S,4R)-4-(2,6-dichloro-purin-9-yl)-cyclopent-2-enyl ester ethyl ester

Product 1

HCID 86643670HCID 86643670, compound

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

A mixture comprising triphenylphosphine (0.299 g, 0.874 mmol) and Pd2(dba)3 (0.267 g, 0.291 mmol) in dry THF (5 mL) under an inert atmosphere of argon is stirred at RT for 10 minutes. This mixture is then added to a pre-stirring mixture of carbonic acid (1S,4R)-4-(2,6-dichloro-purin-9-yl)-cyclopent-2-enyl ester ethyl ester (Intermediate AA2) (2.00 g, 5.83 mmol) and 4-ethyl-2H-[1,2,3]triazole (0.594 g, 6.12 mmol) in THF (15 mL). The resulting mixture is stirred at RT overnight and then concentrated in vacuo. The crude product is purified by chromatography on silica eluting with 0-50% EtOAc in iso-hexane to afford the title compound as a white solid. (MH+ 350).

Workup

  1. concentrationconcentrated in vacuo
  2. customThe crude product is purified by chromatography on silica eluting with 0-50% EtOAc in iso-hexane

Sources & evidence

ORD record
ord-1d4ea045696d4bc38530429a916155ad
Source dataset
uspto-grants-2012_06
Patent number
US08193164B2

Reaction notes

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