Potassium Iodide → 6-[2-(1,3,4,5-tetrahydro-2H-pyrido[4,3-b]-indol-2-yl)ethyl]-2,7-dimethyl-5H-1,3,4-thiadiazolo[3,2-a]pyrimidin-5-one

HRID 380381Notes

Reaction equation

HRID 380381 reaction equation
Cl[CH2:2][CH2:3][C:4]1[C:9](=[O:10])[N:8]2[N:11]=[C:12]([CH3:14])[S:13][C:7]2=[N:6][C:5]=1[CH3:15].[CH2:16]1[C:28]2[C:27]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[NH:21][C:20]=2[CH2:19][CH2:18][NH:17]1.C(=O)(O)[O-].[Na+].[I-].[K+]>C(O)CCC>[CH2:16]1[C:28]2[C:27]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[NH:21][C:20]=2[CH2:19][CH2:18][N:17]1[CH2:2][CH2:3][C:4]1[C:9](=[O:10])[N:8]2[N:11]=[C:12]([CH3:14])[S:13][C:7]2=[N:6][C:5]=1[CH3:15]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 516892Sodium BicarbonateHCID 7232301H,2H,3H,4H,5H-pyrido[4,3-b]indoleHCID 155864606-(2-chloroethyl)-2,7-dimethyl-5H-1,3,4-thiadiazolo[3,2-a]pyrimidin-5-one

Product 1

HCID 186774246-[2-(1,3,4,5-tetrahydro-2H-pyrido[4,3-b]-indol-2-yl)ethyl]-2,7-dimethyl-5H-1,3,4-thiadiazolo[3,2-a]pyrimidin-5-oneYield 28.1%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A mixture of 6-(2-chloroethyl)-2,7-dimethyl-5H-1,3,4-thiadiazolo[3,2-a]pyrimidin-5-one (4.2 g), 1,2,3,4-tetrahydro-5H-pyrido[4,3-b]indole (2.65 g), sodium bicarbonate (2 g), potassium iodide (0.1 g) in 1-butanol (122 ml) was refluxed for 20 hours. The reaction mixture was filtered while hot and the filtrate was evaporated. The residue was purified by column chromatography over silica gel (eluent: CHCl3/CH3OH 95/5). The solvent of the desired fraction was evaporated and the residue was crystallized from acetonitrile, yielding 1.6 g (28.1%) of 6-[2-(l,3,4,5-tetrahydro-2H-pyrido [4,3-b]-indol-2-yl) ethyl]-2,7-dimethyl-5H-1,3,4-thiadiazolo[3,2-a]pyrimidin-5-one (compound 42).

Workup

  1. temperaturewas refluxed for 20 hours
  2. filtrationThe reaction mixture was filtered while hot and the filtrate
  3. customwas evaporated
  4. customThe residue was purified by column chromatography over silica gel (eluent: CHCl3/CH3OH 95/5)
  5. customThe solvent of the desired fraction was evaporated
  6. customthe residue was crystallized from acetonitrile

Sources & evidence

ORD record
ord-f892da1676604a2880ddc6e90d8fd537
Source dataset
uspto-grants-2001_10
Patent number
US06303614B1

Reaction notes

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