Chloroform → 4-[6-Amino-8-(3-fluorophenyl)-2-iodo-9H-9-purinyl]butanoic Acid

HRID 1369384Notes

Reaction equation

HRID 1369384 reaction equation
[NH2:1][C:2]1[N:10]=[C:9]([I:11])[N:8]=[C:7]2[C:3]=1[N:4]=[C:5]([C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([F:23])[CH:18]=1)[N:6]2[CH2:12][CH2:13][CH2:14][CH2:15][OH:16].C(Cl)(Cl)Cl.C(#N)C.I([O-])(=O)(=O)=[O:32].[Na+]>O.[Ru](=O)(=O)(=O)=O.CC(O)C.O>[NH2:1][C:2]1[N:10]=[C:9]([I:11])[N:8]=[C:7]2[C:3]=1[N:4]=[C:5]([C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([F:23])[CH:18]=1)[N:6]2[CH2:12][CH2:13][CH2:14][C:15]([OH:32])=[O:16]

Participants

8

Reactant 4

HCID 6212ChloroformHCID 6342AcetonitrileHCID 221337754-[6-amino-8-(3-fluorophenyl)-2-iodo-9H-9-purinyl]butanolHCID 23667635Sodium periodate

Product 1

HCID 221338964-[6-Amino-8-(3-fluorophenyl)-2-iodo-9H-9-purinyl]butanoic AcidYield 91%

Reagents, catalysts & solvents 3

HCID 86760087Ruthenium tetraoxide hydrateCatalystHCID 962WaterSolventHCID 3776IsopropanolSolvent

Procedure

To 1.50 g of 4-[6-amino-8-(3-fluorophenyl)-2-iodo-9H-9-purinyl]butanol were added 30 ml of chloroform, 30 ml of acetonitrile, 45 ml of water, 73 mg of ruthenium tetraoxide hydrate and 4.10 g of sodium periodate and the mixture was vigorously stirred in a nitrogen stream for 5 hours at room temperature. The reaction was stopped by 2-propanol and the insoluble matters were filtered off followed by washing with 1000 ml of chloroform-methanol (1:1). The filtrate was concentrated, the residue was suspended in water, and the suspension was adjusted to pH 2-3 with 1N hydrochloric acid and the crystals were collected by filtration. The crystals were washed with water and ether to give 1.41 g of the title compound. The yield was 91%.

Workup

  1. filtrationthe insoluble matters were filtered off
  2. washby washing with 1000 ml of chloroform-methanol (1:1)
  3. concentrationThe filtrate was concentrated
  4. filtrationthe crystals were collected by filtration
  5. washThe crystals were washed with water and ether

Sources & evidence

ORD record
ord-14fa8a166cb346209d5fd779a9230ae9
Source dataset
uspto-grants-2003_06
Patent number
US06579868B1

Reaction notes

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