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

HRID 620156Notes

Reaction equation

HRID 620156 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-piperidinopyrimidine (2.89 g) and 2-mercapto-5-methoxybenzimidazole (2.46 g) in ethanol (40 ml) and lN 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-c57b2c3864d04b71895a08da403b1409
Source dataset
uspto-grants-1989_04
Patent number
US04820708

Reaction notes

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