Sodium Hydroxide → N-(4,6-bis-propylamino-[1,3,5]triazin-2-yl)-O-isopropyl-N-methyl-hydroxylamine

HRID 1752128Notes

Reaction equation

HRID 1752128 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][CH2:9][CH2:10][CH3:11])[N:5]=[C:4]([NH:12][CH2:13][CH2:14][CH3:15])[N:3]=1.Cl.[CH:17]([O:20][NH:21][CH3:22])([CH3:19])[CH3:18].[OH-].[Na+]>O1CCOCC1.O>[CH2:13]([NH:12][C:4]1[N:5]=[C:6]([NH:8][CH2:9][CH2:10][CH3:11])[N:7]=[C:2]([N:21]([CH3:22])[O:20][CH:17]([CH3:19])[CH3:18])[N:3]=1)[CH2:14][CH3:15]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 183046-chloro-2-N,4-N-dipropyl-1,3,5-triazine-2,4-diamineHCID 86665980O-isopropyl-N-methyl-hydroxylamine hydrochloride

Product 1

HCID 57377909N-(4,6-bis-propylamino-[1,3,5]triazin-2-yl)-O-isopropyl-N-methyl-hydroxylamineYield 95%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2-chloro-N-(4,6-bis-(n-propylamino)-[1,3,5]triazine (XXXIV) (1.65 g, 16.61 mmol), O-isopropyl-N-methyl-hydroxylamine hydrochloride (LXIII, 2.09 g, 16.61 mmol) and NaOH (0.66 g, 16.61 mmol) in 1,4-dioxane (50 mL) and water (5 mL) was heated at 100° C. for 16 h. The volatiles were then removed under reduced pressure. Saturated NaHCO3 solution (50 mL) was added to the residue and the mixture was extracted with EtOAc (3×50 mL). The combined organic extracts were washed with water (50 mL), brine (50 mL) and dried over Na2SO4. The solvent was removed under reduced pressure and the crude product was purified by flash column chromatography using gradient elution from CH2Cl2/EtOH (99:1) to CH2Cl2/EtOH (95:5) to yield N-(4,6-bis-n-propylamino-[1,3,5]triazin-2-yl)-O-isopropyl-N-methyl-hydroxylamine (LXIV, 1.93 g, 95%). ESI-MS (m/z): 283 [M+H]+.

Workup

  1. customThe volatiles were then removed under reduced pressure
  2. additionSaturated NaHCO3 solution (50 mL) was added to the residue
  3. extractionthe mixture was extracted with EtOAc (3×50 mL)
  4. washThe combined organic extracts were washed with water (50 mL), brine (50 mL)
  5. dry with materialdried over Na2SO4
  6. customThe solvent was removed under reduced pressure
  7. customthe crude product was purified by flash column chromatography
  8. washelution from CH2Cl2/EtOH (99:1) to CH2Cl2/EtOH (95:5)

Sources & evidence

ORD record
ord-77315c72aa89480aae02cc78f1a3722a
Source dataset
uspto-grants-2015_10
Patent number
US09162992B2

Reaction notes

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