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

HRID 2205651Notes

Reaction equation

HRID 2205651 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-c4f401fe30184d859e5cc66732db597f
Source dataset
uspto-grants-2016_06
Patent number
US09371325B2

Reaction notes

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