Urea → HCID 22505874, compound

HRID 907406Notes

Reaction equation

HRID 907406 reaction equation
[OH:1][CH:2]1[CH:6]([CH2:7][OH:8])[O:5][CH:4]([C:9]2C(O)=[N:11][C:12](O)=[C:13]([Cl:15])[N:14]=2)[CH2:3]1.N([O-])=O.[Na+].[NH2:22][C:23]([NH2:25])=O>C(O)(=O)C>[OH:1][CH:2]1[CH:6]([CH2:7][OH:8])[O:5][CH:4]([C:9]2[C:23]([NH2:25])=[N:22][C:12]([NH2:11])=[C:13]([Cl:15])[N:14]=2)[CH2:3]1

Participants

5

Reactant 3

HCID 1176UreaHCID 23668193Sodium NitriteHCID 178520084HCID 178520084, compound

Product 1

HCID 22505874HCID 22505874, compoundYield 88.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

264 mg (1 mmol) 3-(4-Hydroxy-5-hydroxymethyl -tetrahydrofuran-2-yl)-2,6-dihydroxy-5-chloro-pyrazine from example 10 was subjected to a deamination reaction in a mixture of 50 ml 80% acetic acid and 700 mg (10 mmol) NaNO2. After standing for 5 hours at RT, the reaction was almost complete according to TLC. 2 g urea was added to the reaction mixture to destroy excess nitrite and stirred for a further three hours at RT. Afterwards the solution was applied to an activated carbon column (Carboraffin C, ca. 50 ml volume), adequately washed and the desired product was eluted with ethanol/water/ammonium. 230 mg (ca. 87%) of a viscous oil resulted after evaporation which was used in the next stage without further purification.

Workup

  1. customto destroy excess nitrite
  2. washadequately washed
  3. washthe desired product was eluted with ethanol/water/ammonium

Sources & evidence

ORD record
ord-a15381fa2ced4e6cb3b67e20705b8efd
Source dataset
uspto-grants-2011_09
Patent number
US08013147B2

Reaction notes

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