Triphenylphosphine → 2,6-Dichloro-9-cyclopropylpurine

HRID 452580Notes

Reaction equation

HRID 452580 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.C1(P([C:25]2[CH:30]=[CH:29]C=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(O)CC1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>O1CCCC1>[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH:29]2[CH2:30][CH2:25]2)=[C:4]([Cl:11])[N:3]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 123361CyclopropanolHCID 53244122,6-DichloropurineHCID 5363146Diisopropyl azodicarboxylate

Product 1

HCID 836813712,6-Dichloro-9-cyclopropylpurineYield 35%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

2,6-Dichloropurine (1 mmol), triphenylphosphine (1.3 mmol), tetrahydrofurane (5 ml) and cyclopropanol (5 mmol) were stirred at rt under nitrogen to give clear yellowish solution, which was then cooled to 0° C. and diisopropyldiazadicarboxylate (DIAD; 1.3 mmol) was added via syringe. The reaction mixture was then stirred at rt for 12 h. After evaporation of the solvents the product was extracted with diethylether and purified by column chromatography (silicagel, 1% MeOH in CHCl3). Crystallization from methanol gave the product in yield 35%, mp 121-124° C.

Workup

  1. customto give clear yellowish solution, which
  2. customAfter evaporation of the solvents the product
  3. extractionwas extracted with diethylether
  4. custompurified by column chromatography (silicagel, 1% MeOH in CHCl3)
  5. customCrystallization from methanol
  6. customgave the product in yield 35%, mp 121-124° C.

Sources & evidence

ORD record
ord-1588bcbed76247d18f369896691036af
Source dataset
uspto-grants-2013_07
Patent number
US08492391B2

Reaction notes

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