Water → HCID 18919308, compound

HRID 1291430Notes

Reaction equation

HRID 1291430 reaction equation
[Si]([O:8][C:9]1[CH:37]=[CH:36][C:12]([C:13]([C:15]2[CH:35]=[CH:34][C:18]([CH2:19][N:20]3[C:24]4[N:25]=[C:26]([S:32][CH3:33])[N:27]([CH2:30][CH3:31])[C:28](=[O:29])[C:23]=4[CH:22]=[CH:21]3)=[CH:17][CH:16]=2)=[O:14])=[CH:11][CH:10]=1)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C1COCC1.O>C1COCC1>[CH2:30]([N:27]1[C:28](=[O:29])[C:23]2[CH:22]=[CH:21][N:20]([CH2:19][C:18]3[CH:17]=[CH:16][C:15]([C:13](=[O:14])[C:12]4[CH:36]=[CH:37][C:9]([OH:8])=[CH:10][CH:11]=4)=[CH:35][CH:34]=3)[C:24]=2[N:25]=[C:26]1[S:32][CH3:33])[CH3:31]

Participants

5

Reactant 3

HCID 962WaterHCID 11078149TBAF tetrahydrofuranHCID 69959817HCID 69959817, compound

Product 1

HCID 18919308HCID 18919308, compoundYield 93.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In THF (76.8 ml) was dissolved 7-[4-(4-t-butyldimethylsilyloxybenzoyl)benzyl]-3-ethyl-2-methylthio-7H-pyrrolo[2,3-d]pyrimidin-4-one (4.10 g) followed by addition of 1M-tetrabutylammonium fluoride-THF (7.68 ml), and the mixture was stirred for 30 minutes. To this reaction mixture was added water and the THF was distilled off. Then, ethyl acetate was added to the residue and the organic layer was separated. The organic layer was washed with saturated aqueous NaCl solution and dried over anhydrous sodium sulfate and the solvent was then distilled off under reduced pressure. The residue was triturated with ether and the resulting powder was collected by filtration, rinsed with ether, methanol and hexane, and dried to provide the title compound as crystalline powder (3.0 g)

Workup

  1. distillationthe THF was distilled off
  2. additionThen, ethyl acetate was added to the residue
  3. customthe organic layer was separated
  4. washThe organic layer was washed with saturated aqueous NaCl solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationthe solvent was then distilled off under reduced pressure
  7. customThe residue was triturated with ether
  8. filtrationthe resulting powder was collected by filtration
  9. washrinsed with ether, methanol and hexane
  10. customdried

Sources & evidence

ORD record
ord-ec569256b25a4bd48626a8103bc5c964
Source dataset
uspto-grants-1998_05
Patent number
US05753664

Reaction notes

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