2-Chloropyrimidine → 2-Aminobenzimidazole

HRID 280352Notes

Reaction equation

HRID 280352 reaction equation
ClC1N=CC=CN=1.NCCSCC1OC(CN2CCC([NH:25][C:26]3[N:30](CC4C=CC(F)=CC=4)[C:29]4[CH:39]=[CH:40][CH:41]=[CH:42][C:28]=4[N:27]=3)CC2)=CC=1.C(=O)([O-])O.[Na+]>C(O)C>[NH:27]1[C:28]2[CH:42]=[CH:41][CH:40]=[CH:39][C:29]=2[N:30]=[C:26]1[NH2:25]

Participants

5

Reactant 3

HCID 744042-ChloropyrimidineHCID 516892Sodium BicarbonateHCID 13653914HCID 13653914, compound

Product 1

HCID 136242-Aminobenzimidazole

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1.14 parts of 2-chloropyrimidine, 5 parts of N-[1-[[5-[(2-aminoethyl)thiomethyl]-2-furanyl]methyl]-4-piperidinyl]-1-[(4-fluorophenyl)methyl]-1H-benzimidazol-2-amine, 8 parts of sodium hydrogen carbonate and 80 parts of ethanol was stirred and refluxed overnight. The reaction mixture was filtered and the filtrate was evaporated. The residue was purified by column chromatography over silica gel using a mixture of trichloromethane and methanol (97:3 by volume) as eluent. The main fraction was collected and the eluent was evaporated. The residue was crystallized from 1,1'-oxybisethane, yielding 1.2 parts (21%) of 1-[(4-fluorophenyl)methyl]-N-[1-[[5-]]2-(2-pyrimidinylamino)ethyl]thiomethyl]-2-furanyl]methyl]-4-piperidinyl]-1H-benzimidazol-2-amine; mp. 128.9° C. (compound 50).

Workup

  1. temperaturerefluxed overnight
  2. filtrationThe reaction mixture was filtered
  3. customthe filtrate was evaporated
  4. customThe residue was purified by column chromatography over silica gel using
  5. additiona mixture of trichloromethane and methanol (97:3 by volume) as eluent
  6. customThe main fraction was collected
  7. customthe eluent was evaporated
  8. customThe residue was crystallized from 1,1'-oxybisethane

Sources & evidence

ORD record
ord-990a49ae0c0b4ba8b960414c7191798e
Source dataset
uspto-grants-1986_05
Patent number
US04588722

Reaction notes

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