Triphenylphosphine → (1S,4R)-4-(2,6-Dichloro-9H-purin-9-yl)cyclopent-2-en-1-ol

HRID 1882502Notes

Reaction equation

HRID 1882502 reaction equation
[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([NH:6][CH:7]=[N:8]2)=[C:4]([Cl:11])[N:3]=1.CC([O:15][C@H:16]1[CH:20]=[CH:19][C@@H:18](O)[CH2:17]1)=O.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:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[C@@H:19]2[CH2:20][C@H:16]([OH:15])[CH:17]=[CH:18]2)=[C:4]([Cl:11])[N:3]=1

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 53244122,6-DichloropurineHCID 10154103rac-(1R,4S)-4-hydroxycyclopent-2-en-1-yl acetate

Product 1

HCID 10378467(1S,4R)-4-(2,6-Dichloro-9H-purin-9-yl)cyclopent-2-en-1-ol

Reagents, catalysts & solvents 1

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst

Procedure

2,6-Dichloropurine (10 g, 52.90 mmol), (1S,4R)-cis 4-acetoxy-2-cyclopenten-1-ol (10 g. 70.40 mmol), tris(dibenzylideneacetone)dipalladium(0) (3.20 g, 3.50 mmol) and polymer supported triphenylphosphine (3 mmol/g, 11.60 g, 35.00 mmol) are placed in an oven-dried flask under an atmosphere of argon. Dry deoxygenated THF (80 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 50° C. The reaction is shown to be complete by LCMS after 1 hour. The reaction mixture is allowed to cool, filtered and the solvent is removed in vacuo. The title compound is obtained after purification by flash column chromatography (silica, dichloromethane/methanol 25:1). 1H nmr (CDCl3, 400 MHz); 8.30 (s, 1H), 6.40 (m, 1H), 5.90 (m, 1H), 5.50 (m, 1H), 4.95 (m, 1H), 3.05 (m, 1H), 2.10 (m, 1H), MS (ES+) m/e 271 (MH+).

Workup

  1. customare placed in an oven-dried flask under an atmosphere of argon
  2. customDry
  3. customdeoxygenated THF (80 ml)
  4. additionis added
  5. additionTriethylamine (20 ml) is added
  6. stirringthe reaction mixture is stirred at 50° C
  7. waitto be complete by LCMS after 1 hour
  8. temperatureto cool
  9. filtrationfiltered
  10. customthe solvent is removed in vacuo

Sources & evidence

ORD record
ord-86771b05287e4f83a6b2c2b79907c25b
Source dataset
uspto-grants-2012_11
Patent number
US08318750B2

Reaction notes

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