Acetone → Ammonia

HRID 729514Notes

Reaction equation

HRID 729514 reaction equation
[CH:1]12[CH2:7][CH:4]([NH:5][CH2:6]1)[CH2:3][N:2]2[C:8]1[N:13]2[CH:14]=[N:15][N:16]=[C:12]2[CH:11]=[C:10]([C:17]2[CH:22]=[CH:21][N:20]=[C:19]([NH:23][CH:24]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[CH3:25])[CH:18]=2)[N:9]=1.[CH3:32][C:33]([CH3:35])=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)(Cl)Cl.C(Cl)Cl>[NH3:2].[CH:33]([N:5]1[CH2:6][C@@H:1]2[CH2:7][C@H:4]1[CH2:3][N:2]2[C:8]1[N:16]2[N:15]=[CH:14][N:13]=[C:12]2[CH:11]=[C:10]([C:17]2[CH:22]=[CH:21][N:20]=[C:19]([NH:23][C@H:24]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[CH3:25])[CH:18]=2)[N:9]=1)([CH3:35])[CH3:32]

Participants

7

Reactant 3

HCID 180AcetoneHCID 5049666Sodium triacetoxyborohydrideHCID 68910396HCID 68910396, compound

Product 2

HCID 222AmmoniaYield 1%HCID 68905880HCID 68905880, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
70 °C

Procedure

A solution of {4-[5-(2,5-diaza-bicyclo[2.2.1]hept-2-yl)-[1,2,4]triazolo[4,3-c]pyrimidin-7-yl]-pyridin-2-yl}-(1-phenyl-ethyl)-amine (0.25 g, 0.61 mmol) in chloroform (5 mL) were added acetone (1 mL) and sodium triacetoxyborohydride (0.45 g, 2.14 mmol) and stirred at 70° C. for 2 h. Upon cooling to room temperature, the reaction was diluted with methylene chloride and washed with saturated sodium bicarbonate, brine, and dried (K2CO3). Flash chromatography of the crude product with 1% 2M NH3 in MeOH/CHCl3 afforded the title compound as an off-white solid. MS (ES+): 455.2 [M+H]+, 453.2 [M−H]−.

Workup

  1. temperatureUpon cooling to room temperature
  2. washwashed with saturated sodium bicarbonate, brine
  3. dry with materialdried (K2CO3)

Sources & evidence

ORD record
ord-44b46e1db61b49fdbbe40383e72701d4
Source dataset
uspto-grants-2009_09
Patent number
US07582631B2

Reaction notes

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