Sodium Carbonate → HCID 178518040, compound

HRID 256660Notes

Reaction equation

HRID 256660 reaction equation
[O:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[O:4][CH2:3][CH:2]1[CH2:11]O.CC1C=CC(S([O-])(=O)=O)=CC=1.Br.Br.[F:26][C:27]1[CH:32]=[CH:31][C:30]([CH2:33][N:34]2[C:42]3[C:37](=[N:38][CH:39]=[N:40][C:41]=3[OH:43])[N:36]=[C:35]2[CH2:44][CH:45]2[CH2:50][CH2:49][NH:48][CH2:47][CH2:46]2)=[CH:29][CH:28]=1.C(=O)([O-])[O-].[Na+].[Na+]>CN(C)C=O>[O:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[O:4][CH2:3][CH:2]1[CH2:11][N:48]1[CH2:47][CH2:46][CH:45]([CH2:44][C:35]2[N:34]([CH2:33][C:30]3[CH:29]=[CH:28][C:27]([F:26])=[CH:32][CH:31]=3)[C:42]3[C:37](=[N:38][CH:39]=[N:40][C:41]=3[OH:43])[N:36]=2)[CH2:50][CH2:49]1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 131715235HCID 131715235, compoundHCID 178419279HCID 178419279, compound

Product 1

HCID 178518040HCID 178518040, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 3.2 parts of 2,3-dihydro-1,4-benzodioxin-2-methanol 4-methylbenzenesulfonate {ester}. 4.5 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-dimethylformamide 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 1.5 parts (34%) of 8-[[1-[(2,3-dihydro-1,4-benzodioxin-2-yl)methyl]-4-piperidinyl]methyl]-7-[(4-fluorophenyl) methyl]-7H-purin-6-ol; mp. 175.2° C. (compound 59).

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-585671788b34461c890a49d51ed5382c
Source dataset
uspto-grants-1993_11
Patent number
US05258380

Reaction notes

Loading…