Acetone → Ammonia

HRID 729543Notes

Reaction equation

HRID 729543 reaction equation
[CH:1]12[CH2:7][CH:4]([NH:5][CH2:6]1)[CH2:3][N:2]2[C:8]1[N:13]=[C:12]([C:14]2[CH:19]=[CH:18][N:17]=[C:16]([NH:20][C@H:21]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH3:22])[CH:15]=2)[CH:11]=[C:10]([CH3:29])[N:9]=1.[CH3:30][C:31]([CH3:33])=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)(Cl)Cl.C(Cl)Cl>[NH3:2].[CH:31]([N:5]1[CH2:6][CH:1]2[CH2:7][CH:4]1[CH2:3][N:2]2[C:8]1[N:13]=[C:12]([C:14]2[CH:19]=[CH:18][N:17]=[C:16]([NH:20][C@H:21]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH3:22])[CH:15]=2)[CH:11]=[C:10]([CH3:29])[N:9]=1)([CH3:33])[CH3:30]

Participants

7

Reactant 3

HCID 180AcetoneHCID 5049666Sodium triacetoxyborohydrideHCID 57832675HCID 57832675, compound

Product 2

HCID 222AmmoniaYield 1%HCID 57832676HCID 57832676, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
70 °C

Procedure

A solution of 4-(2-(2,5-diaza-bicyclo[2.2.1]heptan-2-yl)-6-methylpyrimidin-4-yl)-N-((S)-1-phenylethyl)pyridin-2-amine (0.23 g, 0.60 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 over anhydrous K2CO3. Flash chromatography of the crude product with 1% 2M NH3 in MeOH/CHCl3 afforded the title compound as a pale yellow solid. MS (ES+): 429[M+H]+,

Workup

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

Sources & evidence

ORD record
ord-2ac0def537264898af5e00190b4b8f96
Source dataset
uspto-grants-2009_09
Patent number
US07582631B2

Reaction notes

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