2-Chloropyrimidine → HCID 14013088, compound

HRID 1904865Notes

Reaction equation

HRID 1904865 reaction equation
Cl[C:2]1[N:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[F:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][N:16]2[C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=3[N:18]=[C:17]2[CH2:25][CH:26]2[CH2:31][CH2:30][N:29]([CH2:32][CH2:33][NH:34][CH3:35])[CH2:28][CH2:27]2)=[CH:11][CH:10]=1.C(=O)([O-])O.[Na+]>C(O)C>[F:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][N:16]2[C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=3[N:18]=[C:17]2[CH2:25][CH:26]2[CH2:27][CH2:28][N:29]([CH2:32][CH2:33][N:34]([CH3:35])[C:2]3[N:7]=[CH:6][CH:5]=[CH:4][N:3]=3)[CH2:30][CH2:31]2)=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 744042-ChloropyrimidineHCID 516892Sodium BicarbonateHCID 14013298HCID 14013298, compound

Product 1

HCID 14013088HCID 14013088, compoundYield 76.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1.8 parts of 2-chloropyrimidine, 6 parts of 4-[[1-[(4-fluorophenyl)methyl]-1H-benzimidazol-2-yl]methyl]-N-methyl-1-piperidineethanamine, 1.7 parts of sodium hydrogen carbonate and 120 parts of ethanol was stirred and refluxed overnight. The reaction mixture was evaporated. Water was added. The product was extracted with 4-methyl-2-pentanone. The extract was dried, filtered and evaporated. The residue was crystallized from a mixture of 2,2'-oxybispropane and 1,1'-oxybisethane (50:50 by volume). The product was filtered off and dried, yielding 5.5 parts (76.5%) of N-[2-[4-[[1-[(4-fluorophenyl)methyl]-1H-benzimidazol-2-yl]methyl]-1-piperidinyl]ethyl]-N-methyl-2-pyrimidinamine; mp. 135.4° C. (514).

Workup

  1. temperaturerefluxed overnight
  2. customThe reaction mixture was evaporated
  3. additionWater was added
  4. extractionThe product was extracted with 4-methyl-2-pentanone
  5. customThe extract was dried
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was crystallized from a mixture of 2,2'-oxybispropane and 1,1'-oxybisethane (50:50 by volume)
  9. filtrationThe product was filtered off
  10. customdried

Sources & evidence

ORD record
ord-8db6825ac3e54e588747b54d1a116276
Source dataset
uspto-grants-1989_06
Patent number
US04839374

Reaction notes

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