Urea → HCID 22505874, compound

HRID 2186439Notes

Reaction equation

HRID 2186439 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-5f7ba932da1d48b6b7ee9d0349df3069
Source dataset
uspto-grants-2002_06
Patent number
US06403786B1

Reaction notes

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