Triphenylphosphine → 2,6-Dichloro-9-(tetrahydrofuran-3-ylmethyl)-9H-purine

HRID 421305Notes

Reaction equation

HRID 421305 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.[O:12]1[CH2:16][CH2:15][CH:14]([CH2:17]O)[CH2:13]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>O1CCCC1>[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH2:17][CH:14]2[CH2:15][CH2:16][O:12][CH2:13]2)=[C:4]([Cl:11])[N:3]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 139980Tetrahydro-3-furanmethanolHCID 53244122,6-Dichloropurine

Product 1

HCID 593335962,6-Dichloro-9-(tetrahydrofuran-3-ylmethyl)-9H-purineYield 142.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

2,6-Dichloropurine (21 g, 113 mmol) and (tetrahydrofuran-3-yl)methanol (11.5 g, 113 mmol) were dissolved in tetrahydrofuran (250 ml) followed by the dropwise addition of triphenylphosphine (33 g, 125 mmol) and a diisopropyl azodicarboxylate (24.5 ml, 125 mmol)-tetrahydrofuran (50 ml) solution with ice cooling and the resulting mixture was stirred at room temperature for 2 hours. The solvent was concentrated under reduced pressure and then the residue was purified by silica gel chromatography (hexane:ethyl acetate=5:1 to 1:1 to 0:1) to give the title compound (44 g) as a pale yellow oil.

Workup

  1. concentrationThe solvent was concentrated under reduced pressure
  2. customthe residue was purified by silica gel chromatography (hexane:ethyl acetate=5:1 to 1:1 to 0:1)

Sources & evidence

ORD record
ord-aa8d9829c9664bebbfb0ab09be8f9732
Source dataset
uspto-grants-2012_01
Patent number
US08097622B2

Reaction notes

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