Potassium Iodide → 6-(2-(4-(1H-Indol-3-yl)piperidin-1-yl)ethyl)-3,7-dimethyl-5H-thiazolo(3,2-a)pyrimidin-5-one

HRID 371102Notes

Reaction equation

HRID 371102 reaction equation
Cl[CH2:2][CH2:3][C:4]1[C:9](=[O:10])[N:8]2[C:11]([CH3:14])=[CH:12][S:13][C:7]2=[N:6][C:5]=1[CH3:15].[NH:16]1[CH2:21][CH2:20][CH:19]([C:22]2[C:30]3[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=3)[NH:24][CH:23]=2)[CH2:18][CH2:17]1.C(=O)([O-])[O-].[Na+].[Na+].[I-].[K+]>O.CC(C)CC(=O)C>[NH:24]1[C:25]2[C:30](=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:22]([CH:19]2[CH2:20][CH2:21][N:16]([CH2:2][CH2:3][C:4]3[C:9](=[O:10])[N:8]4[C:11]([CH3:14])=[CH:12][S:13][C:7]4=[N:6][C:5]=3[CH3:15])[CH2:17][CH2:18]2)=[CH:23]1

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 10340Sodium CarbonateHCID 7022353-(4-Piperidinyl)-1H-indoleHCID 134778116-(2-Chloroethyl)-3,7-dimethyl-5H-[1,3]thiazolo[3,2-a]pyrimidin-5-one

Product 1

HCID 30861076-(2-(4-(1H-Indol-3-yl)piperidin-1-yl)ethyl)-3,7-dimethyl-5H-thiazolo(3,2-a)pyrimidin-5-one

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 7909Methyl Isobutyl KetoneSolvent

Procedure

A mixture of 3.75 parts of 6-(2-chloroethyl)-3,7-dimethyl-5H-thiazolo[3,2-a]pyrimidin-5-one, 3 parts of 3-(4-piperidinyl)-1H-indole, 10 parts of sodium carbonate, 0.1 parts of potassium iodide and 200 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 (90:10 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was crystallized from ethanol, yielding 3.25 parts of 6-[2-[4-(1H-indol-3-yl)-1-piperidinyl]ethyl]-3,7-dimethyl-5H-thiazolo[3,2-a]pyrimidin-5-one; mp. 274.7° C. (compound 11).

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 (90:10 by volume) as eluent
  6. customThe pure fractions were collected
  7. customthe eluent was evaporated
  8. customThe residue was crystallized from ethanol

Sources & evidence

ORD record
ord-67c276bf42aa43719bec30ef6d4fbf06
Source dataset
uspto-grants-1985_07
Patent number
US04529727

Reaction notes

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