2,6-Dichlorobenzyl chloride → HCID 22398446, compound

HRID 912602Notes

Reaction equation

HRID 912602 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([Cl:10])[C:3]=1[CH2:4]Cl.[Mg].[Cl:12][C:13]1[N:18]=[C:17](Cl)[CH:16]=[C:15]([Cl:20])[N:14]=1>BrCCBr>[Cl:12][C:13]1[N:14]=[C:15]([Cl:20])[CH:16]=[C:17]([CH2:4][C:3]2[C:2]([Cl:1])=[CH:9][CH:8]=[CH:7][C:6]=2[Cl:10])[N:18]=1

Participants

5

Reactant 3

HCID 748322,6-Dichlorobenzyl chlorideHCID 773782,4,6-TrichloropyrimidineHCID 5462224Magnesium2×

Product 1

HCID 22398446HCID 22398446, compoundYield 21%

Reagents, catalysts & solvents 1

HCID 78391,2-DibromoethaneCatalyst

Procedure

A solution of 2,6-dichlorobenzylchloride (0.102 mol) in 1,1-diethylether (10 ml) was added dropwise to magnesium (0.102 mol) in 1,1-diethylether (60 ml). The reaction was initiated by adding 2 drops of 1,2-dibromoethane. After most of magnesium disappeared, 2,4,6-trichloropyrimidine (0.051 mol) in 1,1-diethylether (30 ml) was added. The mixture was stirred overnight at room temperature. The solvent was evaporated and the residue was purified by flash column chromatography over silica gel (eluent: CH2Cl2/hexane 1/2). The desired fractions were collected and the solvent was evaporated, yielding 3.3 g of (21%) 2,4-dichloro-6-[(2,6-dichloro-phenyl)methyl]pyrimidine (interm. 1; m.p.: 106-107° C.). b) Intermediate (1) (0.0081 mol) in 2-propanol (100 ml) was heated until complete dissolution. The solution was then transferred into a pressure tube and NH3 gas was bubbled into it for 20 minutes. Then the mixture was heated to 80° C. for 16 hours. The solvent was evaporated, yielding a residue of two compounds: 2-chloro-6-[(2,6-di-chloro-phenyl)methyl]-4-pyrimidinamine (interm. 2) and 4-chloro-6-[(2,6-dichloro-phenyl)methyl]-2-pyrimidinamine (interm. 3).

Workup

  1. customThe solvent was evaporated
  2. customthe residue was purified by flash column chromatography over silica gel (eluent: CH2Cl2/hexane 1/2)
  3. customThe desired fractions were collected
  4. customthe solvent was evaporated

Sources & evidence

ORD record
ord-f854d7387ab74629ac0e06a4bb4a8723
Source dataset
uspto-grants-2011_09
Patent number
US08026248B2

Reaction notes

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