Dichloromethane → N,N-dibenzyl-6-chloro-5-nitropyrimidin-4-amine

HRID 1041915Notes

Reaction equation

HRID 1041915 reaction equation
[CH2:1]([NH:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ClCCl.[Cl:19][C:20]1[C:25]([N+:26]([O-:28])=[O:27])=[C:24](Cl)[N:23]=[CH:22][N:21]=1.C(N(CC)CC)C>O>[CH2:9]([N:8]([CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:24]1[C:25]([N+:26]([O-:28])=[O:27])=[C:20]([Cl:19])[N:21]=[CH:22][N:23]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 6344Dichloromethane2×HCID 7656DibenzylamineHCID 8471TriethylamineHCID 203124,6-Dichloro-5-nitropyrimidine

Product 1

HCID 23477266N,N-dibenzyl-6-chloro-5-nitropyrimidin-4-amineYield 105%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Dibenzylamine (10.2 g) in a dichloromethane (30 mL) solution was added dropwise on an ice bath to a dichloromethane (70 mL) solution of 4,6-dichloro-5-nitropyrimidine (10 g). This was followed by the addition of triethylamine (14.4 mL) and stirring for 1 hour. Water was then added to the reaction mixture and the organic layer was subsequently washed with saturated aqueous sodium chloride solution and dried over anhydrous sodium sulfate. The solvent was concentrated under reduced pressure to obtain the title compound (19.2 g) having the physical property value indicated below.

Workup

  1. washthe organic layer was subsequently washed with saturated aqueous sodium chloride solution
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationThe solvent was concentrated under reduced pressure

Sources & evidence

ORD record
ord-e7e77e3a67504ea2addbe56e56e5f2cd
Source dataset
uspto-grants-2013_10
Patent number
US08557803B2

Reaction notes

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