Cyclopentanol → 2,6-dichloro-9-cyclopentyl-9H-purine

HRID 33357

Reaction equation

HRID 33357 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.[CH:12]1(O)[CH2:16][CH2:15][CH2:14][CH2:13]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1>[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH:12]2[CH2:16][CH2:15][CH2:14][CH2:13]2)=[C:4]([Cl:11])[N:3]=1

Participants

6

Reactant 4

HCID 7298CyclopentanolHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 53244122,6-Dichloropurine

Product 1

HCID 108011162,6-dichloro-9-cyclopentyl-9H-purine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Dissolve 2,6-dichloropurine (1, 680 mg, 3.60 mmol), cyclopentanol (2a, 260 mg, 3.02 mmol), and triphenyl phosphine (950 mg, 3.60 mmol) in dry THF (20 mL) and cool to 0° C. Add diethyl azodicarboxylate (DEAD, 570 μL, 3.60 mmol) dropwise over a period of 15 minutes under a nitrogen atmosphere. Stir the resulting solution for 60 hours at room temperature. Evaporate the solvent in vacuo, charge directly onto a 500 g silica gel column, and elute with DCM and concentrate the desired fractions to give 2,6-dichloro-9-cyclopentyl-9H-purine (3a).

Workup

  1. customEvaporate the solvent in vacuo
  2. additioncharge directly onto a 500 g silica gel column
  3. washelute with DCM
  4. concentrationconcentrate the desired fractions

Sources & evidence

ORD record
ord-5c9e493c4f094a12bec8c930814c2959
Source dataset
uspto-grants-2008_09
Patent number
US07429595B2

Linked notes

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