Hydrogen Peroxide → HCID 178467464, compound

HRID 1178221Notes

Reaction equation

HRID 1178221 reaction equation
[NH2:1][C:2]1[N:11]=[C:10]([O:12][CH2:13][CH3:14])[C:9]2[C:4](=[N:5][CH:6]=[CH:7][N:8]=2)[N:3]=1.[OH:15]O>FC(F)(F)C(O)=O>[NH2:1][C:2]1[N:11]=[C:10]([O:12][CH2:13][CH3:14])[C:9]2[C:4](=[N:5][CH:6]=[CH:7][N:8]=2)[N+:3]=1[O-:15]

Participants

4

Reactant 2

HCID 784Hydrogen Peroxide2×HCID 113675134-Ethoxypteridin-2-amine

Product 1

HCID 178467464HCID 178467464, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

To a cooled (0° C.) solution of the compound of example 60 (2.47 g, 12.9 mmoles) in trifluoroacetic acid (53 ml) was added dropwise 2.53 ml of a 35% aqueous H2O2 solution. The reaction mixture was kept at 4° C. for two days in the refrigerator, whereby another 1.25 ml of the same H2O2 solution was added after 1 day. The solution was concentrated in vacuo. The residue was suspended in water and neutralized by the addition of a concentrated ammonia solution. Evaporation of the solvent in vacuo and purification of the residue by flash chromatography (silica, using a CH3OH/CH2Cl2 mixture (6:94) as the eluent) provided the title compound as a yellow powder (861 mg, yield: 32%). Mass spectrum data are as follows: m/z (%): 230 ([M+Na]+, 30), 208 ([M+H]+, 100), 180 [(M+H-ethene)+, 10].

Workup

  1. concentrationThe solution was concentrated in vacuo
  2. additionneutralized by the addition of a concentrated ammonia solution
  3. customEvaporation of the solvent
  4. customin vacuo and purification of the residue by flash chromatography (silica

Sources & evidence

ORD record
ord-87b5c50b7ed2400082763d97e7f2c274
Source dataset
uspto-grants-2007_10
Patent number
US07276506B2

Reaction notes

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