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

HRID 727063Notes

Reaction equation

HRID 727063 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-38baae26d0734afcb327abdeb062fdb2
Source dataset
uspto-grants-1998_01
Patent number
US05712276

Reaction notes

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