2-Chloropyrimidine → HCID 178515786, compound

HRID 1534743Notes

Reaction equation

HRID 1534743 reaction equation
Cl[C:2]1[N:7]=[CH:6][CH:5]=[CH:4][N:3]=1.Br.Br.Br.[NH2:11][CH2:12][CH2:13][N:14]1[CH2:19][CH2:18][CH:17]([NH:20][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)[CH2:16][CH2:15]1.C(=O)([O-])O.[Na+]>C(O)C>[N:3]1[CH:4]=[CH:5][CH:6]=[N:7][C:2]=1[NH:11][CH2:12][CH2:13][N:14]1[CH2:19][CH2:18][CH:17]([NH:20][C:21]2[NH:25][C:24]3[CH:34]=[CH:35][C:36]([OH:38])=[CH:37][C:23]=3[N:22]=2)[CH2:16][CH2:15]1

Participants

5

Reactant 3

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

Product 1

HCID 178515786HCID 178515786, compound

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]-1H-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-b5c022c4f2444151a77052c998707ad5
Source dataset
uspto-grants-1992_02
Patent number
USRE033833

Reaction notes

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