Methanol → methyl 4-[6-amino-8-(3-fluorophenyl)-2-iodo-9H-9-purinyl]butanoate

HRID 1369385Notes

Reaction equation

HRID 1369385 reaction equation
S(Cl)(Cl)=O.[NH2:5][C:6]1[N:14]=[C:13]([I:15])[N:12]=[C:11]2[C:7]=1[N:8]=[C:9]([C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([F:28])[CH:23]=1)[N:10]2[CH2:16][CH2:17][CH2:18][C:19]([OH:21])=[O:20].[CH3:29]O>>[NH2:5][C:6]1[N:14]=[C:13]([I:15])[N:12]=[C:11]2[C:7]=1[N:8]=[C:9]([C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([F:28])[CH:23]=1)[N:10]2[CH2:16][CH2:17][CH2:18][C:19]([O:21][CH3:29])=[O:20]

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 221338964-[6-Amino-8-(3-fluorophenyl)-2-iodo-9H-9-purinyl]butanoic Acid

Product 1

HCID 22133918methyl 4-[6-amino-8-(3-fluorophenyl)-2-iodo-9H-9-purinyl]butanoateYield 100%

Conditions

Temperature
2.5 °C

Procedure

Thionyl chloride (1.2 ml) was added dropwise into a mixture of 1.41 g of 4-[6-amino-8-(3-fluorophenyl)-2-iodo-9H-9-purinyl]butanoic acid and 75 ml of methanol over 15 minutes during the mixture was stirred at 0-5° C. in a nitrogen stream. This was raised to room temperature and stirred for 45 minutes and the solvent was evaporated. The resulting residue was dissolved in ethyl acetate and then the solution was washed with a saturated aqueous solution of sodium bicarbonate twice and then with brine once. The organic layer was dried over anhydrous sodium sulfate and concentrated to give 1.45 g of the title compound. The yield was 100%.

Workup

  1. temperatureThis was raised to room temperature
  2. stirringstirred for 45 minutes
  3. customthe solvent was evaporated
  4. dissolutionThe resulting residue was dissolved in ethyl acetate
  5. washthe solution was washed with a saturated aqueous solution of sodium bicarbonate twice
  6. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-cdb629fe10bc4558afa8a38608a62fd7
Source dataset
uspto-grants-2003_06
Patent number
US06579868B1

Reaction notes

Loading…