HCID 19705068, compound → HCID 19705127, compound

HRID 235021Notes

Reaction equation

HRID 235021 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 (500ml) 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 NaHCO3 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-98ea896645174d868a74762d742f2db8
Source dataset
uspto-grants-1997_01
Patent number
US05597828

Reaction notes

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