Allyl Alcohol → HCID 178479934, compound

HRID 1826542Notes

Reaction equation

HRID 1826542 reaction equation
N[C:2]1[N:10]=[C:9]([C:11]#[C:12][C:13]2([OH:18])[CH2:17][CH2:16][CH2:15][CH2:14]2)[N:8]=[C:7]2[C:3]=1[N:4]=[C:5]([C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([F:26])[CH:21]=1)[N:6]2[CH3:19].C([OH:30])C=C.[OH-].[Na+]>C1COCC1>[F:26][C:22]1[CH:21]=[C:20]([C:5]2[N:6]([CH3:19])[C:7]3[C:3]([N:4]=2)=[C:2]([OH:30])[N:10]=[C:9]([C:11]#[C:12][C:13]2([OH:18])[CH2:17][CH2:16][CH2:15][CH2:14]2)[N:8]=3)[CH:25]=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 7858Allyl AlcoholHCID 14798Sodium HydroxideHCID 98413641-(2-(6-amino-8-(3-fluorophenyl)-9-methyl-9H-2-purinyl)-1-ethynyl)-1-cyclopentanol

Product 1

HCID 178479934HCID 178479934, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 50 mg of 1-{2-[6-amino-8-(3-fluorophenyl)-9-methyl-9H-2-purinyl]-1-ethynyl}-1-cyclopentanol were added 3.0 ml of allyl alcohol and 1.0 ml of 5M NaOH, the mixture was stirred at room temperature for 10 minutes, 1.0 ml of THF was added thereto and the mixture was stirred again at room temperature for 15 hours and 40 minutes. The solvent was evaporated and then 200 ml of ethyl acetate and water (1:1) were added and an extraction was carried out. The aqueous lyaer was extracted with 100 ml of ethyl acetate again and the all organic layers were combined and washed with water and with brine once each. The organic layer was dried over anhydrous sodium sulfate and the solvent was evaporated. The resulting residue was purified by a p-TLC (CH2Cl2:MeOH=10:1), the resulting yellowish white crystals were suspended in diethyl ether and the suspenion was filtered to give 217 mg of the title compound as white crystals. The yield was 36%.

Workup

  1. stirringthe mixture was stirred again at room temperature for 15 hours and 40 minutes
  2. customThe solvent was evaporated
  3. addition200 ml of ethyl acetate and water (1:1) were added
  4. extractionan extraction
  5. extractionThe aqueous lyaer was extracted with 100 ml of ethyl acetate again
  6. washwashed with water and with brine once each
  7. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  8. customthe solvent was evaporated
  9. customThe resulting residue was purified by a p-TLC (CH2Cl2:MeOH=10:1)
  10. filtrationthe suspenion was filtered

Sources & evidence

ORD record
ord-10312eaaad2d4619a7dcc122bfc9b857
Source dataset
uspto-grants-2006_05
Patent number
USRE039112E1

Reaction notes

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