Ammonium Hydroxide → HCID 11174185, compound

HRID 1295554Notes

Reaction equation

HRID 1295554 reaction equation
[CH3:1][C@@:2]1([OH:26])[C@H:6]([OH:7])[C@@H:5]([CH2:8][OH:9])[O:4][C@H:3]1[N:10]1[C:14]2[N:15]=[CH:16][N:17]=[C:18]([NH2:19])[C:13]=2[C:12]([C:20]#[C:21][Si](C)(C)C)=[CH:11]1.[NH4+].[OH-]>CO>[CH3:1][C@@:2]1([OH:26])[C@H:6]([OH:7])[C@@H:5]([CH2:8][OH:9])[O:4][C@H:3]1[N:10]1[C:14]2[N:15]=[CH:16][N:17]=[C:18]([NH2:19])[C:13]=2[C:12]([C:20]#[CH:21])=[CH:11]1

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 11383309HCID 11383309, compound

Product 1

HCID 11174185HCID 11174185, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The title compound from Example 2 (0.040 g, 0.0132 mmol) was dissolved in methanol and NH4OH was added and the mixture left at ambient temperature for 1 hour. The solvent was evaporated, the residue dissolved in methanol and co-evaporated with silica gel. Dry silica was loaded on the glass filter with silica gel and the desilylated compound was eluted with acetone. Solvent was evaporated and the residue crystallized from methanol/acetonitrile to provide for 7-(2′-C-methyl-β-D-ribofuranosyl)-4-amino-5-(ethyn-1-yl)-pyrrolo[2,3-d]pyrimidine.

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe residue dissolved in methanol and co-evaporated with silica gel
  3. filtrationfilter with silica gel
  4. washthe desilylated compound was eluted with acetone
  5. customSolvent was evaporated
  6. customthe residue crystallized from methanol/acetonitrile

Sources & evidence

ORD record
ord-813215915c7b487e8f8ff141680d51f0
Source dataset
uspto-grants-2007_07
Patent number
US07244713B2

Reaction notes

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