Sodium Carbonate → 6-[2-[4-(4-fluorobenzoyl)-1-piperidinyl]ethyl]-2,3,7-trimethyl-5H-thiazolo[3,2-a]pyrimidin-5-one

HRID 325927Notes

Reaction equation

HRID 325927 reaction equation
Br.Br[CH2:3][CH2:4][C:5]1[C:10](=[O:11])[N:9]2[C:12]([CH3:16])=[C:13]([CH3:15])[S:14][C:8]2=[N:7][C:6]=1[CH3:17].Cl.[F:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]([CH:28]2[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]2)=[O:27])=[CH:22][CH:21]=1.C(=O)([O-])[O-].[Na+].[Na+].C[O-].[Na+]>O.CC(C)CC(=O)C>[F:19][C:20]1[CH:21]=[CH:22][C:23]([C:26]([CH:28]2[CH2:33][CH2:32][N:31]([CH2:3][CH2:4][C:5]3[C:10](=[O:11])[N:9]4[C:12]([CH3:16])=[C:13]([CH3:15])[S:14][C:8]4=[N:7][C:6]=3[CH3:17])[CH2:30][CH2:29]2)=[O:27])=[CH:24][CH:25]=1

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 3084438p-Fluorophenyl 4-piperidyl ketone hydrochlorideHCID 10942334Sodium MethoxideHCID 155864696-(2-bromoethyl)-2,3,7-trimethyl-5H-thiazolo[3,2-a]pyrimidin-5-one monohydrobromide

Product 1

HCID 155864336-[2-[4-(4-fluorobenzoyl)-1-piperidinyl]ethyl]-2,3,7-trimethyl-5H-thiazolo[3,2-a]pyrimidin-5-one

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 7909Methyl Isobutyl KetoneSolvent

Procedure

A mixture of 5.85 parts of 6-(2-bromoethyl)-2,3,7-trimethyl-5H-thiazolo[3,2-a]pyrimidin-5-one monohydrobromide, 4 parts of (4-fluorophenyl) (4-piperidinyl)methanone hydrochloride, 10 parts of sodium carbonate, 3 parts of a sodium methoxide solution 30% and 240 parts of 4-methyl-2-pentanone was stirred and refluxed for 20 hours using a water-separator. The reaction mixture was filtered hot over Hyflo and the filtrate was evaporated. The residue was purified by column-chromatography over silica gel using a mixture of trichloromethane and methanol (95:5 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was crystallized from a mixture of acetonitrile and 2,2'-oxybispropane (3:1 by volume) yielding 1 part of 6-[2-[4-(4-fluorobenzoyl)-1-piperidinyl]ethyl]-2,3,7-trimethyl-5H-thiazolo[3,2-a]pyrimidin-5-one; mp. 159.0° C. (compound 24).

Workup

  1. temperaturerefluxed for 20 hours
  2. filtrationThe reaction mixture was filtered hot over Hyflo
  3. customthe filtrate was evaporated
  4. customThe residue was purified by column-chromatography over silica gel using
  5. additiona mixture of trichloromethane and methanol (95:5 by volume) as eluent
  6. customThe pure fractions were collected
  7. customthe eluent was evaporated
  8. customThe residue was crystallized from a mixture of acetonitrile and 2,2'-oxybispropane (3:1 by volume)

Sources & evidence

ORD record
ord-91360494dbb248fea4592843d3339e5c
Source dataset
uspto-grants-1984_04
Patent number
US04443451

Reaction notes

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