Hydrogen Bromide → 5-bromo-N-methyl-N-(tetrahydro-2H-pyran-4-yl)pyridin-2-amine

HRID 57551Notes

Reaction equation

[CH3:1][N:2]([CH:10]1[CH2:15][CH2:14][O:13][CH2:12][CH2:11]1)[C:3]1[CH:8]=[CH:7][C:6](N)=[CH:5][N:4]=1.N([O-])=O.[Na+].[OH-].[Na+].[BrH:22]>O>[Br:22][C:6]1[CH:7]=[CH:8][C:3]([N:2]([CH3:1])[CH:10]2[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)=[N:4][CH:5]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of N2-methyl-N2-(tetrahydro-2H-pyran-4-yl)pyridine-2,5-diamine (150 mg, 0.73 mmol) in 2 mL of aq HBr was added a solution of NaNO2 (55 mg, 0.80 mmol) in 1 mL of H2O at 0° C. Then the mixture was stirred at 0° C. for 40 minutes. After that, the mixture was poured into a solution of CuBr (220 mg, 1.53 mmol) in 2 mL aq HBr at 0° C., the reaction was heated to 60° C. and stirred for 2 hours. After cooling, the mixture was based with 2M NaOH to pH=8-9 and extracted with EA, washed with H2O and brine, dried and concentrated, purified on TLC (EA:PE=1:1) to give white solid. MS (m/z): 273 (M+H)+

Workup

temperaturethe reaction was heated to 60° C.
stirringstirred for 2 hours
temperatureAfter cooling
extractionextracted with EA
washwashed with H2O and brine
customdried
concentrationconcentrated
custompurified on TLC (EA:PE=1:1)
customto give white solid

Sources & evidence

ORD record: ord-92f8ad19765a4c6d83f297479fb24959
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09434726B2

Reaction notes

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