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

HRID 846380Notes

Reaction equation

HRID 846380 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-f326a576f3b6494db45120a33d80fcbf
Source dataset
uspto-grants-1992_08
Patent number
US05136080

Reaction notes

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