Triphenylphosphine → 2,6-Dichloro-9-[(1R,4S)-4-(5-ethyl-tetrazol-2-yl)-cyclopent-2-enyl]-9H-purine

HRID 1641887Notes

Reaction equation

HRID 1641887 reaction equation
C(OC(=O)O[C@H:6]1[CH2:10][C@@H:9]([N:11]2[CH:19]=[N:18][C:17]3[C:12]2=[N:13][C:14]([Cl:21])=[N:15][C:16]=3[Cl:20])[CH:8]=[CH:7]1)C.[CH2:23]([C:25]1[N:26]=[N:27][NH:28][N:29]=1)[CH3:24].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)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.[Pd].[Pd]>[Cl:21][C:14]1[N:13]=[C:12]2[C:17]([N:18]=[CH:19][N:11]2[C@@H:9]2[CH2:10][C@H:6]([N:27]3[N:28]=[N:29][C:25]([CH2:23][CH3:24])=[N:26]3)[CH:7]=[CH:8]2)=[C:16]([Cl:20])[N:15]=1

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 2234645-ethyl-1H-1,2,3,4-tetrazoleHCID 58025019Carbonic acid (1S,4R)-4-(2,6-dichloro-purin-9-yl)-cyclopent-2-enyl ester ethyl ester

Product 1

HCID 866228002,6-Dichloro-9-[(1R,4S)-4-(5-ethyl-tetrazol-2-yl)-cyclopent-2-enyl]-9H-purine

Reagents, catalysts & solvents 1

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst

Procedure

Carbonic acid (1S,4R)-4-(2,6-dichloro-purin-9-yl)-cyclopent-2-enyl ester ethyl ester (Intermediate AC) (3 g, 8.75 mmol), 5-Ethyl-2H-tetrazole (0.94 g. 9.62 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.40 g, 0.44 mmol) and triphenylphosphine (0.35 g, 1.32 mmol) are placed in an oven-dried flask under an atmosphere of argon. Dry deoxygenated THF (40 mL) is added and the reaction mixture is stirred gently for 5 minutes. Triethylamine (20 mL) is added and the reaction mixture is stirred at room temperature for 1 hour. The reaction mixture is allowed to cool and the solvent is removed in vacuo. The residue was taken up in methanol (50 mL) and the solid was filtered off-product. 1H nmr (CDCl3, 400 MHz); 8.55 (s, 1H), 6.35 (m, 1H), 6.25 (m, 1H), 6.05 (m, 1H), 5.90 (m, 1H), 3.45 (m, 1H), 2.85 (q, 2H), 2.30 (m, 1H), 1.30 (t, 3H), MS (ES+) m/e 351 (MH+).

Workup

  1. customDry
  2. customdeoxygenated THF (40 mL)
  3. additionis added
  4. additionTriethylamine (20 mL) is added
  5. stirringthe reaction mixture is stirred at room temperature for 1 hour
  6. temperatureto cool
  7. customthe solvent is removed in vacuo
  8. filtrationthe solid was filtered off-product

Sources & evidence

ORD record
ord-62eef1ad4ff34c8e8e8eb09f40b29bb8
Source dataset
uspto-grants-2012_02
Patent number
US08114877B2

Reaction notes

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