Sodium Bicarbonate → 5-Bromo-N3-[1-(tetrahydro-2H-pyran-4-yl)ethyl]pyridine-2,3-diamine

HRID 1625985Notes

Reaction equation

HRID 1625985 reaction equation
[NH2:1][C:2]1[C:7]([NH2:8])=[CH:6][C:5]([Br:9])=[CH:4][N:3]=1.[O:10]1[CH2:15][CH2:14][CH:13]([C:16](=O)[CH3:17])[CH2:12][CH2:11]1.C([BH3-])#N.[Na+].C(=O)(O)[O-].[Na+]>CO.C(O)(=O)C>[Br:9][C:5]1[CH:6]=[C:7]([NH:8][CH:16]([CH:13]2[CH2:14][CH2:15][O:10][CH2:11][CH2:12]2)[CH3:17])[C:2]([NH2:1])=[N:3][CH:4]=1

Participants

7

Reactant 4

HCID 516892Sodium BicarbonateHCID 6911565-Bromopyridine-2,3-diamineHCID 5003444Sodium cyanoborohydrideHCID 98773651-(Tetrahydro-2H-pyran-4-yl)ethanone

Product 1

HCID 866523695-Bromo-N3-[1-(tetrahydro-2H-pyran-4-yl)ethyl]pyridine-2,3-diamineYield 19.6%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

2,3-Diamino-5-bromopyridine (1.07 g) and 1-(tetrahydro-2H-pyran-4-yl)ethanone (0.80 g) were dissolved in methanol (20 ml), and acetic acid (0.98 ml) was added. After stirring at room temperature for a while, sodium cyanoborohydride (1.08 g) was added and the mixture was stirred at room temperature for 20 hours. A saturated aqueous sodium bicarbonate solution was added to the reaction solution, followed by extraction with ethyl acetate. Then, the organic layer was dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The resulting residue was purified by flash column chromatography (developed with ethyl acetate-hexane) to give the title compound (334 mg).

Workup

  1. additionwas added
  2. extractionfollowed by extraction with ethyl acetate
  3. dry with materialThen, the organic layer was dried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customThe resulting residue was purified by flash column chromatography (developed with ethyl acetate-hexane)

Sources & evidence

ORD record
ord-14c64c082ffb43ca93d362306b63ca45
Source dataset
uspto-grants-2014_07
Patent number
US08785438B2

Reaction notes

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