Nitric Acid → 2-Amino-6-methyl-5-nitropyrimidin-4-ol

HRID 1516832

Reaction equation

HRID 1516832 reaction equation
[NH2:1][C:2]1[NH:7][C:6](=[O:8])[CH:5]=[C:4]([CH3:9])[N:3]=1.[N+:10]([O-])([OH:12])=[O:11].C(OCC)C>OS(O)(=O)=O>[NH2:1][C:2]1[NH:7][C:6](=[O:8])[C:5]([N+:10]([O-:12])=[O:11])=[C:4]([CH3:9])[N:3]=1

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 3283Diethyl EtherHCID 1354020552-Amino-6-methylpyrimidin-4-one

Product 1

HCID 1354603042-Amino-6-methyl-5-nitropyrimidin-4-olYield 81%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

To a mixture of 2-amino-6-methylpyrimidin-4(3H)-one (50 g, 0.4 mol) in 250 mL of H2SO4 at 0° C. was added 40 mL of HNO3 with an additional funnel. After being stirred at room temperature for 3 h, the reaction mixture was slowly poured into 3.6 L of diethyl ether and stirred for 15 min. Decant the ether solution and added 1.0 L of ethyl acetate to the solid and stirred for 10 h. The solid (54.8 g, 81% yield) was filtered and used for next step without any further purification.

Workup

  1. stirringstirred for 15 min
  2. customDecant the ether solution
  3. additionadded 1.0 L of ethyl acetate to the solid
  4. stirringstirred for 10 h

Sources & evidence

ORD record
ord-403c33fc10664467971bca8db27ad35f
Source dataset
uspto-grants-2012_07
Patent number
US08227601B2

Linked notes

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