Hydroxylamine → n-Hydroxypyrimidine-5-carboximidamide

HRID 450657Notes

Reaction equation

HRID 450657 reaction equation
[N:1]1[CH:6]=[C:5]([C:7]#[N:8])[CH:4]=[N:3][CH:2]=1.[NH2:9][OH:10]>CO>[OH:10][N:9]=[C:7]([C:5]1[CH:6]=[N:1][CH:2]=[N:3][CH:4]=1)[NH2:8]

Participants

4

Reactant 2

HCID 787HydroxylamineHCID 10197646Pyrimidine-5-carbonitrile

Product 1

HCID 34181140n-Hydroxypyrimidine-5-carboximidamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of the product of Example 79B (5.47 g, 52 mmol) and aqueous hydroxylamine (Aldrich, 50%, 2.3 mL, 78 mmol) in methanol (50 mL) was stirred at 65° C. for 1 hour and then concentrated under reduced pressure to remove the volatiles. The residue was triturated with EtOAc (30 mL). The precipitates were collected by filtration and dried to give the titled compound. 1H NMR (300 MHz, DMSO-d6) δ 6.14 (s, 2 H), 9.03 (s, 2 H), 9.18 (s, 1 H), 10.06 (s, 1 H) ppm; MS (DCI/NH3) m/z 139 (M+H)+, 156 (M+NH4)+.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customto remove the volatiles
  3. customThe residue was triturated with EtOAc (30 mL)
  4. filtrationThe precipitates were collected by filtration
  5. customdried

Sources & evidence

ORD record
ord-8d52a1a81ffc4d33b9f90b9335ab3c5c
Source dataset
uspto-grants-2013_07
Patent number
US08486979B2

Reaction notes

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