Hydroxylamine → n-Hydroxypyrimidine-5-carboximidamide

HRID 578148Notes

Reaction equation

HRID 578148 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, 2H), 9.03 (s, 2H), 9.18 (s, 1H), 10.06 (s, 1H) 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-915e37e6bcc4409e9a30b95a1fe6e99b
Source dataset
uspto-grants-2015_05
Patent number
US09040568B2

Reaction notes

Loading…