Sodium hydride → 9-[(4-fluorophenyl)methyl]-8-[[1-(phenylmethyl)-4-piperidinyl]oxy]-9H-purine

HRID 256648Notes

Reaction equation

HRID 256648 reaction equation
[C:1]1([CH2:7][N:8]2[CH2:13][CH2:12][CH:11]([OH:14])[CH2:10][CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].CN(C)C(=O)C.[F:23][C:24]1[CH:29]=[CH:28][C:27]([CH2:30][N:31]2[C:39](SC)=[N:38][C:37]3[C:32]2=[N:33][CH:34]=[N:35][CH:36]=3)=[CH:26][CH:25]=1>O>[F:23][C:24]1[CH:29]=[CH:28][C:27]([CH2:30][N:31]2[C:39]([O:14][CH:11]3[CH2:12][CH2:13][N:8]([CH2:7][C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)[CH2:9][CH2:10]3)=[N:38][C:37]3[C:32]2=[N:33][CH:34]=[N:35][CH:36]=3)=[CH:26][CH:25]=1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 31374DimethylacetamideHCID 784611-Benzylpiperidin-4-olHCID 197852329-[(4-fluorophenyl)methyl]-8-(methylthio)-9H-purine

Product 1

HCID 197852369-[(4-fluorophenyl)methyl]-8-[[1-(phenylmethyl)-4-piperidinyl]oxy]-9H-purineYield 61.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 12.6 parts of 1-(phenylmethyl)-4-piperidinol, 3.2 parts of a sodium hydride dispersion 50% and 200 parts of N,N-dimethylacetamide was stirred for 1 hour at room temperature. 18 Parts of 9-[(4-fluorophenyl)methyl]-8-(methYlthio)-9H-purine were added portionwise and upon completion, stirring was continued for 4 hours at room temperature. The reaction mixture was poured into water. The product was filtered off and taken up in trichloromethane. The organic layer was washed with water and filtered over diatomaceous earth. The filtrate was dried, filtered and evaporated. After crystallization from acetonitrile, the product was filtered off and dried, yielding 16.75 parts (61.1%) of 9-[(4-fluorophenyl)methyl]-8-[[1-(phenylmethyl)-4-piperidinyl]oxy]-9H-purine; mp. 117.0° C. (compound 5).

Workup

  1. stirringstirring
  2. waitwas continued for 4 hours at room temperature
  3. filtrationThe product was filtered off
  4. washThe organic layer was washed with water
  5. filtrationfiltered over diatomaceous earth
  6. customThe filtrate was dried
  7. filtrationfiltered
  8. customevaporated
  9. customAfter crystallization from acetonitrile
  10. filtrationthe product was filtered off
  11. customdried

Sources & evidence

ORD record
ord-619cbb9fa50c4f2d9e3ef47a0deb49d2
Source dataset
uspto-grants-1993_11
Patent number
US05258380

Reaction notes

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