HCID 19705068, compound → HCID 19705127, compound

HRID 846384Notes

Reaction equation

HRID 846384 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 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-67496ece9b584168a38bb8be29d03568
Source dataset
uspto-grants-1992_08
Patent number
US05136080

Reaction notes

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