2-(Chloromethyl)-4-(piperidin-1-yl)pyrimidine → HCID 178488127, compound

HRID 867878Notes

Reaction equation

HRID 867878 reaction equation
Cl[CH2:2][C:3]1[N:8]=[C:7]([N:9]2[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)[CH:6]=[CH:5][N:4]=1.[SH:15][C:16]1[NH:17][C:18]2[CH:24]=[C:23]([O:25][CH3:26])[CH:22]=[CH:21][C:19]=2[N:20]=1>C(O)C.[OH-].[Na+]>[CH3:26][O:25][C:23]1[CH:22]=[CH:21][C:19]2[NH:20][C:16]([S:15][CH2:2][C:3]3[N:8]=[C:7]([N:9]4[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]4)[CH:6]=[CH:5][N:4]=3)=[N:17][C:18]=2[CH:24]=1

Participants

5

Reactant 2

HCID 143061332-(Chloromethyl)-4-(piperidin-1-yl)pyrimidineHCID 178488032HCID 178488032, compound

Product 1

HCID 178488127HCID 178488127, compoundYield 72.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

A mixture of 2-chloromethyl-4-piperidino-pyrimidine (2.89 g) and 2-mercapto-5-methoxybenzimidazole (2.46 g) in ethanol (40 ml) and 1N sodium hydroxide (15 ml) was stirred at room temperature for 16 hours. After stripping the residue was washed with water and recrystallised from acetonitrile to give 5-methoxy-2-(4-piperidino-2-pyrimidinylmethylthio)-(1H)-benzimidazole (3.5 g) m.p. 145°-147°.

Workup

  1. washwas washed with water
  2. customrecrystallised from acetonitrile

Sources & evidence

ORD record
ord-fa4ff782cb5542498c78e9069a85370d
Source dataset
uspto-grants-1988_10
Patent number
US04777172

Reaction notes

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