Methanol → 9-[(4-fluorophenyl)methyl]-6-methoxy-8-[[1-(phenylmethyl)-4-piperidinyl]methyl]-9H-purine

HRID 256676Notes

Reaction equation

HRID 256676 reaction equation
[CH3:1][O-:2].[Na+].[Na].CO.Cl[C:8]1[N:16]=[CH:15][N:14]=[C:13]2[C:9]=1[N:10]=[C:11]([CH2:25][CH:26]1[CH2:31][CH2:30][N:29]([CH2:32][C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[CH2:28][CH2:27]1)[N:12]2[CH2:17][C:18]1[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=1>O>[F:24][C:21]1[CH:22]=[CH:23][C:18]([CH2:17][N:12]2[C:11]([CH2:25][CH:26]3[CH2:31][CH2:30][N:29]([CH2:32][C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=4)[CH2:28][CH2:27]3)=[N:10][C:9]3[C:13]2=[N:14][CH:15]=[N:16][C:8]=3[O:2][CH3:1])=[CH:19][CH:20]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 5360545SodiumHCID 10942334Sodium MethoxideHCID 197852696-chloro-9-[(4-fluorophenyl)methyl]-8-[[1-(phenylmethyl)-4-piperidinyl]methyl]-9H-purine

Product 1

HCID 197852459-[(4-fluorophenyl)methyl]-6-methoxy-8-[[1-(phenylmethyl)-4-piperidinyl]methyl]-9H-purineYield 70.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a previously prepared sodium methoxide solution, starting from 25 parts of sodium in 400 parts of methanol, were added 49.4 parts of 6-chloro-9-[(4-fluorophenyl)methyl]-8-[[1-(phenylmethyl)-4-piperidinyl]methyl]-9H-purine. After stirring for 8 hours at reflux temperature, the reaction mixture was cooled and 1000 parts of water were added. The precipitated product was filtered off and dried, yielding 34.5 parts (70.4%) of 9-[(4-fluorophenyl)methyl]-6-methoxy-8-[[1-(phenylmethyl)-4-piperidinyl]methyl]-9H-purine (compound 184).

Workup

  1. temperatureat reflux temperature
  2. temperaturethe reaction mixture was cooled
  3. filtrationThe precipitated product was filtered off
  4. customdried

Sources & evidence

ORD record
ord-e7937ef16b4248acac02118c7758eb8e
Source dataset
uspto-grants-1993_11
Patent number
US05258380

Reaction notes

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