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

HRID 1497998

Reaction equation

HRID 1497998 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.[Cl:16][C:17]1[C:22]([N+:23]([O-:25])=[O:24])=[C:21](Cl)[N:20]=[CH:19][N:18]=1.C(N(CC)CC)C.O>ClCCl>[CH2:9]([N:8]([CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:21]1[C:22]([N+:23]([O-:25])=[O:24])=[C:17]([Cl:16])[N:18]=[CH:19][N:20]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 962WaterHCID 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 6344DichloromethaneSolvent2×

Procedure

A solution of dibenzylamine (10.2 g) in dichloromethane (30 mL) was dripped into a solution of 4,6-dichloro-5-nitropyrimidine (10 g) in dichloromethane (70 mL) on an ice bath. Then triethylamine (14.4 mL) was added, and the mixture was stirred for 1 hour. Water was added to the reaction mixture, the organic layer was washed with a saturated aqueous sodium chloride solution and dried over anhydrous sodium sulfate, and the solvent was concentrated under reduced pressure to obtain the title compound (19.2 g) with the physical property value shown below.

Workup

  1. washthe organic layer was washed with a 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-80a5aff0fd7441ccbf318f407ae418f3
Source dataset
uspto-grants-2015_12
Patent number
US09199997B2

Linked notes

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