2-Chloropyrimidine → 2-Pyrimidinamine, N-(1-(1-((4-fluorophenyl)methyl)-1H-benzimidazol-2-yl)-4-piperidinyl)-

HRID 1165921Notes

Reaction equation

HRID 1165921 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][N:9]2[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=3[N:11]=[C:10]2[N:18]2[CH2:23][CH2:22][CH:21]([NH2:24])[CH2:20][CH2:19]2)=[CH:4][CH:3]=1.Cl[C:26]1[N:31]=[CH:30][CH:29]=[CH:28][N:27]=1.C(=O)(O)[O-].[Na+]>C(O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][N:9]2[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=3[N:11]=[C:10]2[N:18]2[CH2:23][CH2:22][CH:21]([NH:24][C:26]3[N:31]=[CH:30][CH:29]=[CH:28][N:27]=3)[CH2:20][CH2:19]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 744042-ChloropyrimidineHCID 516892Sodium BicarbonateHCID 110127714-Piperidinamine, 1-[1-[(4-fluorophenyl)methyl]-1H-benzimidazol-2-yl]-

Product 1

HCID 30657042-Pyrimidinamine, N-(1-(1-((4-fluorophenyl)methyl)-1H-benzimidazol-2-yl)-4-piperidinyl)-

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1.71 g (0.005 mole) of 1-{1-[(4-fluorophenyl)methyl]-1H-benzimidazol-2-yl}-4-piperidinamine, 0.57 g (0.005 mole) of 2-chloropyrimidine, 0.43 g (0.052 mole) of sodium bicarbonate and 19 ml of ethanol is brought to reflux temperature for 2 days and 2 nights. The mixture is evaporated to dryness, and water and 2N sodium hydroxide are added. The product is taken up with methylene chloride, decanted and washed with water. The product is chromatographed on a silica column (eluent: dichloromethane/methanol, 47:3).

Workup

  1. temperatureto reflux temperature for 2 days
  2. custom2 nights
  3. customThe mixture is evaporated to dryness, and water and 2N sodium hydroxide
  4. additionare added
  5. customdecanted
  6. washwashed with water
  7. customThe product is chromatographed on a silica column (eluent: dichloromethane/methanol, 47:3)

Sources & evidence

ORD record
ord-c56f10dac4c140179138516cfa7558c6
Source dataset
uspto-grants-1990_03
Patent number
US04912219

Reaction notes

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