Methanamine, N-methoxy-, hydrochloride (1:1) → N2-Methoxy-N2-methyl-N4-propyl-1,3,5-triazine-2,4,6-triamine
Reaction equation
[NH2:1][C:2]1[N:7]=[C:6](Cl)[N:5]=[C:4]([NH:9][CH2:10][CH2:11][CH3:12])[N:3]=1.Cl.[CH3:14][NH:15][O:16][CH3:17].CCN(C(C)C)C(C)C>CCO>[NH2:1][C:2]1[N:7]=[C:6]([N:15]([CH3:14])[O:16][CH3:17])[N:5]=[C:4]([NH:9][CH2:10][CH2:11][CH3:12])[N:3]=1Participants
5
Conditions
- Temperature
- 100 °C
Procedure
A mixture of 6-amino-2-chloro-4-n-propylamino-[1,3,5]triazine (XXXVIII) (5 g, 26.65 mmol), N,O-dimethylhydroxylamine hydrochloride (13 g, 133.24 mmol) and DIPEA (27.5 g, 213.2 mmol) in EtOH (100 mL) was heated at 100° C. for 16 h, after which time the solvent was removed under reduced pressure. The residue was dissolved in EtOAc (400 mL), which was washed with water (200 mL) and then with a brine solution (200 mL) and finally dried over Na2SO4. The solvent was removed under reduced pressure to yield N-(6-amino-4-n-propylamino-[1,3,5]triazin-2-yl)-N,O-dimethyl-hydroxylamine (XXXIX) as a white solid (5 g, 89% yield). LCMS (ESI) m/z=213 (M+H)+.
Workup
- customafter which time the solvent was removed under reduced pressure
- dissolutionThe residue was dissolved in EtOAc (400 mL)
- washwhich was washed with water (200 mL)
- dry with materialwith a brine solution (200 mL) and finally dried over Na2SO4
- customThe solvent was removed under reduced pressure
Sources & evidence
- ORD record
- ord-4e376dc0abc242408572130d018d7335
- Source dataset
- uspto-grants-2016_05
- Patent number
- US09351972B2
Reaction notes
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