Sodium Carbonate → HCID 178490261, compound

HRID 256661Notes

Reaction equation

HRID 256661 reaction equation
Cl[CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][CH:5]=1.Br.Br.[F:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21][N:22]2[C:30]3[C:25](=[N:26][CH:27]=[N:28][C:29]=3[OH:31])[N:24]=[C:23]2[CH2:32][CH:33]2[CH2:38][CH2:37][NH:36][CH2:35][CH2:34]2)=[CH:17][CH:16]=1.C(=O)([O-])[O-].[Na+].[Na+]>CN(C)C(=O)C>[F:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21][N:22]2[C:30]3[C:25](=[N:26][CH:27]=[N:28][C:29]=3[OH:31])[N:24]=[C:23]2[CH2:32][CH:33]2[CH2:34][CH2:35][N:36]([CH2:2][CH2:3][C:4]3[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][CH:5]=3)[CH2:37][CH2:38]2)=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 875134-(2-Chloroethyl)phenyl methyl etherHCID 178419279HCID 178419279, compound

Product 1

HCID 178490261HCID 178490261, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 1.9 parts of 1-(2-chloroethyl)-4-methoxybenzene, 5 parts of 7-[(4-fluorophenyl)methyl]-8-(4-piperidinylmethyl)-7H-purin-6-ol dihydrobromide, 4 parts of sodium carbonate and 45 parts of N,N-dimethylacetamide was stirred overnight at 70° C. After cooling, the reaction mixture was filtered over diatomaceous earth and the filtrate was evaporated. The residue was purified by column chromatography over silica gel using a mixture of trichloromethane and methanol, saturated with ammonia, (95:5 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was crystallized from acetontrile. The product was filtered off and dried, yielding 2.2 parts (46%) of 7-[(4-fluorophenyl)methyl]-8-[[1-[2-(4-methoxyphenyl)ethyl]-4-piperidinyl]methyl]-7H-purin-6-ol; mp. 122.2° C. (compound 62).

Workup

  1. temperatureAfter cooling
  2. filtrationthe reaction mixture was filtered over diatomaceous earth
  3. customthe filtrate was evaporated
  4. customThe residue was purified by column chromatography over silica gel using
  5. additiona mixture of trichloromethane and methanol
  6. customThe pure fractions were collected
  7. customthe eluent was evaporated
  8. customThe residue was crystallized from acetontrile
  9. filtrationThe product was filtered off
  10. customdried

Sources & evidence

ORD record
ord-18416eccbffd471688449dc1b47b91b2
Source dataset
uspto-grants-1993_11
Patent number
US05258380

Reaction notes

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