2-Chloropyrimidine → 5-Hydroxybenzimidazole

HRID 845791Notes

Reaction equation

HRID 845791 reaction equation
ClC1N=CC=CN=1.Br.Br.Br.NCCN1CCC(N[C:21]2[N:25](CC3C=CC(F)=CC=3)[C:24]3[CH:34]=[CH:35][C:36]([OH:38])=[CH:37][C:23]=3[N:22]=2)CC1.C(=O)([O-])O.[Na+]>C(O)C>[N:25]1[C:24]2[CH:34]=[CH:35][C:36]([OH:38])=[CH:37][C:23]=2[NH:22][CH:21]=1

Participants

5

Reactant 3

HCID 744042-ChloropyrimidineHCID 516892Sodium BicarbonateHCID 13588089HCID 13588089, compound

Product 1

HCID 30825335-Hydroxybenzimidazole

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1.7 parts of 2-chloropyrimidine, 9.66 parts of 2-[[1-(2-aminoethyl)-4-piperidinyl]amino]-1-[(4-fluorophenyl)methyl]-1H-benzimidazol-5-ol trihydrobromide, 5 parts of sodium hydrogen carbonate and 80 parts of ethanol was stirred and refluxed overnight. The reaction mixture was evaporated and the residue was taken up in trichloromethane. The organic phase was washed with water, dried, filtered and evaporated. The residue was crystallized from a mixture of acetonitrile and methanol, yielding 5.2 parts (83%) of 1-[(4-fluorophenyl)methyl]-2-[[1-[2-(2-pyrimidinylamino)ethyl]-4-piperidinyl]amino]-1e,uns/H/ -benzimidazol-5-ol; mp. 194.4° C. (compound 64).

Workup

  1. temperaturerefluxed overnight
  2. customThe reaction mixture was evaporated
  3. washThe organic phase was washed with water
  4. customdried
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was crystallized from a mixture of acetonitrile and methanol

Sources & evidence

ORD record
ord-7dbe30312a14415999b3b7c3ffd6e780
Source dataset
uspto-grants-1988_07
Patent number
US04760074

Reaction notes

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