Potassium Iodide → HCID 21968276, compound

HRID 1106510Notes

Reaction equation

HRID 1106510 reaction equation
Cl[CH2:2][CH2:3][C:4]1[C:9](=[O:10])[N:8]2[CH:11]=[CH:12][CH:13]=[CH:14][C:7]2=[N:6][C:5]=1[CH3:15].[C:16]1([CH2:22][N:23]2[C:31]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[C@H:25]3[CH2:32][NH:33][CH2:34][CH2:35][C@@H:24]23)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(=O)([O-])[O-].[Na+].[Na+].[I-].[K+]>C(C(C)=O)C(C)C>[C:16]1([CH2:22][N:23]2[C:31]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[C@H:25]3[CH2:32][N:33]([CH2:2][CH2:3][C:4]4[C:9](=[O:10])[N:8]5[CH:11]=[CH:12][CH:13]=[CH:14][C:7]5=[N:6][C:5]=4[CH3:15])[CH2:34][CH2:35][C@@H:24]23)[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 10340Sodium CarbonateHCID 8178663-(2-Chloroethyl)-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-oneHCID 70000476HCID 70000476, compound

Product 1

HCID 21968276HCID 21968276, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 7909Methyl Isobutyl KetoneSolvent

Procedure

A mixture of 3-(2-chloroethyl)-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one (2.45 g), disclosed in EP-0,196,132, intermediate 5 (2.7 g), sodium carbonate (3.3 g) and potassium iodide (0.1 g) in methyl isobutyl ketone (250 ml) was stirred and refluxed for 18 hours. The reaction mixture was cooled, filtered and the filtrate was evaporated. The residue was purified by column chromatography over silica gel (eluent: CHCl3 /CH3OH 90/10). The pure fractions were collected and the solvent was evaporated. The residue was crystallized from ACN (25 ml). The crystals were filtered off and dried, yielding 2.3 g (50%) of (±)-cis-3-[2-[1,3,4,4a,5,9b-hexahydro-5-(phenylmethyl)-2H-pyrido[4,3-b]indol-2-yl]ethyl]-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one (compound 9, mp. 145.1° C.).

Workup

  1. temperaturerefluxed for 18 hours
  2. temperatureThe reaction mixture was cooled
  3. filtrationfiltered
  4. customthe filtrate was evaporated
  5. customThe residue was purified by column chromatography over silica gel (eluent: CHCl3 /CH3OH 90/10)
  6. customThe pure fractions were collected
  7. customthe solvent was evaporated
  8. customThe residue was crystallized from ACN (25 ml)
  9. filtrationThe crystals were filtered off
  10. customdried

Sources & evidence

ORD record
ord-5874a4115e534db1981a0e084ff358fc
Source dataset
uspto-grants-2000_05
Patent number
US06057325

Reaction notes

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