HCID 19705068, compound → HCID 19705127, compound

HRID 727067Notes

Reaction equation

HRID 727067 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([NH2:8])[C:5]([C:9]2[CH:14]=[C:13]([N+:15]([O-])=O)[CH:12]=[CH:11][C:10]=2[Cl:18])=[C:4]([CH3:19])[N:3]=1>C(O)(=O)C.O=[Pt]=O>[NH2:1][C:2]1[N:7]=[C:6]([NH2:8])[C:5]([C:9]2[CH:14]=[C:13]([NH2:15])[CH:12]=[CH:11][C:10]=2[Cl:18])=[C:4]([CH3:19])[N:3]=1

Participants

4

Reactant 1

HCID 19705068HCID 19705068, compound

Product 1

HCID 19705127HCID 19705127, compound

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 176Acetic AcidSolvent

Procedure

A solution of 2,4-diamino-5-(2-chloro-5-nitrophenyl)-6-methyl pyrimidine (13.9 g) in acetic acid (500 ml) was reduced under an atmosphere of hydrogen in the presence of PtO2 (0.28 g). The mixture was filtered through hyflo and the filtrate was concentrated. The residue was neutralised with saturated HaHCO3 solution and the product was extracted with ethyl acetate, bulked, dried (MgSO4) and evaporated. Chromatography on SiO2 gel, eluting with CHCl3 to 40% MeOH/CHCl3, gave the desired product, 6 g, mp. 117°-121° C.

Workup

  1. filtrationThe mixture was filtered through hyflo
  2. concentrationthe filtrate was concentrated
  3. extractionthe product was extracted with ethyl acetate
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. washChromatography on SiO2 gel, eluting with CHCl3 to 40% MeOH/CHCl3

Sources & evidence

ORD record
ord-d3b6d6c75048431493f28da374102d88
Source dataset
uspto-grants-1998_01
Patent number
US05712276

Reaction notes

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