2,4-Diamino-5-(2,3-dichloro-4-nitrophenyl)-6-methylpyrimidine → 2,4-Diamino-5-(2,3,4-trichlorophenyl)-6-methylpyrimidine

HRID 232617Notes

Reaction equation

HRID 232617 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([NH2:8])[C:5]([C:9]2[CH:14]=[CH:13][C:12]([N+]([O-])=O)=[C:11]([Cl:18])[C:10]=2[Cl:19])=[C:4]([CH3:20])[N:3]=1.CO.C(Cl)(Cl)[Cl:24]>Cl[Cu]>[NH2:1][C:2]1[N:7]=[C:6]([NH2:8])[C:5]([C:9]2[CH:14]=[CH:13][C:12]([Cl:24])=[C:11]([Cl:18])[C:10]=2[Cl:19])=[C:4]([CH3:20])[N:3]=1

Participants

4

Reactant 2

HCID 197050312,4-Diamino-5-(2,3-dichloro-4-nitrophenyl)-6-methylpyrimidineHCID 21584188Chloroform methanol

Product 1

HCID 197050562,4-Diamino-5-(2,3,4-trichlorophenyl)-6-methylpyrimidine

Reagents, catalysts & solvents 1

HCID 62652Cuprous chlorideCatalyst

Procedure

This compound was made from the compound of Example 47 by reduction to the amine (PtO2, H2, AcOH), formation of the diazonium salt (NaNO2, H2SO4), and reaction of this with CuCl (as for Example 57). Sublimes at 275° C. Homogenous on TLC (methanol/chloroform, 1:9) Rf=0.36.

Workup

  1. customat 275° C

Sources & evidence

ORD record
ord-a7a6ca636ab746b6bfbd470ca6112a82
Source dataset
uspto-grants-1997_01
Patent number
US05591746

Reaction notes

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