Potassium Iodide → 6-[2-[4-(1H-benzimidazol-2-ylamino)-1-piperidinyl]-ethyl]-1,7-dimethylimidazo[1,2-a]pyrimidin-5(1H)-one

HRID 1085076Notes

Reaction equation

HRID 1085076 reaction equation
Cl[CH2:2][CH2:3][C:4]1[C:9](=[O:10])[N:8]2[CH:11]=[CH:12][N:13]([CH3:14])[C:7]2=[N:6][C:5]=1[CH3:15].Br.Br.[NH:18]1[CH2:23][CH2:22][CH:21]([NH:24][C:25]2[NH:29][C:28]3[CH:30]=[CH:31][CH:32]=[CH:33][C:27]=3[N:26]=2)[CH2:20][CH2:19]1.C(=O)([O-])[O-].[Na+].[Na+].[I-].[K+]>CN(C)C(=O)C>[NH:26]1[C:27]2[CH:33]=[CH:32][CH:31]=[CH:30][C:28]=2[N:29]=[C:25]1[NH:24][CH:21]1[CH2:22][CH2:23][N:18]([CH2:2][CH2:3][C:4]2[C:9](=[O:10])[N:8]3[CH:11]=[CH:12][N:13]([CH3:14])[C:7]3=[N:6][C:5]=2[CH3:15])[CH2:19][CH2:20]1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 10340Sodium CarbonateHCID 19100910HCID 19100910, compoundHCID 22036968N-(Piperidin-4-yl)-1H-benzo[d]imidazol-2-amine dihydrobromide

Product 1

HCID 200614606-[2-[4-(1H-benzimidazol-2-ylamino)-1-piperidinyl]-ethyl]-1,7-dimethylimidazo[1,2-a]pyrimidin-5(1H)-oneYield 86.3%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 11.3 parts of 6-(2-chloroethyl)-1,7-dimethylimidazo[1,2-a]pyrimidin-5(1H)-one (interm. 15), 18.9 parts of N-(4-piperidinyl)-1H-benzimidazol-2-amine dihydrobromide, 16 parts of sodium carbonate, 0.01 parts of potassium iodide and 376 parts of N,N-dimethylacetamide was stirred overnight at 70° C. The reaction mixture was filtered and the filtrate was evaporated. The residue was taken up in a mixture of water, dichloromethane and methanol. The organic layer was separated and the aqueous layer was re-extracted with a mixture of dichloromethane and methanol. The combined organic layers were dried, filtered and evaporated. The residue was crystallized from ethanol, yielding 17.5 parts (86.3%) of 6-[2-[4-(1H-benzimidazol-2-ylamino)-1-piperidinyl]-ethyl]-1,7-dimethylimidazo[1,2-a]pyrimidin-5(1H)-one; mp. 229.5° C. (comp. 80).

Workup

  1. filtrationThe reaction mixture was filtered
  2. customthe filtrate was evaporated
  3. additionThe residue was taken up in a mixture of water, dichloromethane and methanol
  4. customThe organic layer was separated
  5. extractionthe aqueous layer was re-extracted with a mixture of dichloromethane and methanol
  6. customThe combined organic layers were dried
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue was crystallized from ethanol

Sources & evidence

ORD record
ord-31229b23340c47dcbdcdc7a71fe337c6
Source dataset
uspto-grants-1991_04
Patent number
US05008268

Reaction notes

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