Benzylethanolamine → 2-[Benzyl({3-chloro-5-[methyl(1-methylethyl)amino]pyrazin-2-yl}methyl)amino]ethanol

HRID 1877827Notes

Reaction equation

HRID 1877827 reaction equation
C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[Cl:15][C:16]1[C:17]([CH:27]=O)=[N:18][CH:19]=[C:20]([N:22]([CH3:26])[CH:23]([CH3:25])[CH3:24])[N:21]=1.[CH2:29]([NH:36][CH2:37][CH2:38][OH:39])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C.C(OCC)(=O)C.C(O)(=O)C>[CH2:29]([N:36]([CH2:27][C:17]1[C:16]([Cl:15])=[N:21][C:20]([N:22]([CH3:26])[CH:23]([CH3:24])[CH3:25])=[CH:19][N:18]=1)[CH2:37][CH2:38][OH:39])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

8

Reactant 4

HCID 4348BenzylethanolamineHCID 11430Potassium CarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 86648985HCID 86648985, compound

Product 1

HCID 866489842-[Benzyl({3-chloro-5-[methyl(1-methylethyl)amino]pyrazin-2-yl}methyl)amino]ethanolYield 107.5%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

Sodium triacetoxyborohydride (12.8 g) was added to a solution of 3-chloro-5-[methyl(1-methylethyl)amino]pyrazine-2-carbaldehyde (8.6 g), N-benzylethanolamine (7.3 g) and acetic acid (6.9 mL) in acetonitrile (86 mL), and the mixture was stirred at room temperature for 5 hr. To the reaction mixture were added ethyl acetate and 2M aqueous potassium carbonate solution (86 mL), and the aqueous layer was extracted with ethyl acetate. The combined organic layer was washed with water and saturated brine, dried over magnesium sulfate, and concentrated. The residue was purified by basic silica gel column chromatography (solvent gradient: 10→30% ethyl acetate/hexane) to give the title compound (15.1 g, quantitative) as a pale-yellow oil.

Workup

  1. extractionthe aqueous layer was extracted with ethyl acetate
  2. washThe combined organic layer was washed with water and saturated brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by basic silica gel column chromatography (solvent gradient: 10→30% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-adaf3e7a199448cb90e503a57b6d6142
Source dataset
uspto-grants-2012_11
Patent number
US08314088B2

Reaction notes

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