Triphenylphosphine → HCID 22563860, compound

HRID 33361Notes

Reaction equation

HRID 33361 reaction equation
[CH:1]1(O)[CH2:5][CH2:4][CH:3]=[CH:2]1.[Cl:7][C:8]1[N:16]=[C:15]2[C:11]([NH:12][CH:13]=[N:14]2)=[C:10]([Cl:17])[N:9]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1>[Cl:7][C:8]1[N:16]=[C:15]2[C:11]([N:12]=[CH:13][N:14]2[CH:1]2[CH2:5][CH2:4][CH:3]=[CH:2]2)=[C:10]([Cl:17])[N:9]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 2201642-Cyclopentene-1-olHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 53244122,6-Dichloropurine

Product 1

HCID 22563860HCID 22563860, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Add to a stirred solution of 2-cyclopenten-1-ol (2c 2.60 g, 30.9 mmol), 2,6-dichloropurine (1, 7.00 g, 37.0 mmol) and triphenyl phosphine (9.70 g, 37.0 mmol) in dry THF (120 ml) at 0° C., diethyl azodicarboxylate (5.85 ml, 37.0 mmol) dropwise over a period of 15 min. under a nitrogen atmosphere. Stir the resulting solution for 60 hrs at room temperature. Concentrate the reaction mixture, charge the residue directly onto a silica gel column and elute with hexane:ethyl acetate (3:1) to give of 2,6-dichloro-9-cyclopent-2-enyl-9H-purine (3c) (3.20 g, 41%.)

Workup

  1. concentrationConcentrate the reaction mixture
  2. additioncharge the residue directly onto a silica gel column
  3. washelute with hexane:ethyl acetate (3:1)

Sources & evidence

ORD record
ord-0167ac65c2af4e35ace4fd5d5e64ec48
Source dataset
uspto-grants-2008_09
Patent number
US07429595B2

Reaction notes

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