Sodium Carbonate → HCID 178518040, compound

HRID 2248812Notes

Reaction equation

HRID 2248812 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

Conditions

Temperature
70 °C

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 acetonitrile. 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 acetonitrile
  9. filtrationThe product was filtered off
  10. customdried

Sources & evidence

ORD record
ord-b6ce7c9e7fce4454bb344fa47adce938
Source dataset
uspto-grants-1991_08
Patent number
US05041448

Reaction notes

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