Acetaldehyde → HCID 117899620, compound

HRID 522295Notes

Reaction equation

HRID 522295 reaction equation
Cl.[CH3:2][C:3]1[N:4]([CH3:33])[C:5]2[C:10]([N:11]=1)=[C:9]([C:12]1[CH:17]=[CH:16][C:15]([O:18][CH2:19][CH2:20][CH:21]3[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]3)=[C:14]([C:27]([F:30])([F:29])[F:28])[CH:13]=1)[N:8]=[C:7]([C:31]#[N:32])[N:6]=2.[C:34](O[BH-](OC(=O)C)OC(=O)C)(=O)[CH3:35].[Na+].C(=O)C.C([O-])(O)=O.[Na+]>ClC(Cl)C.C(Cl)(Cl)Cl.C(O)(=O)C.C(N(CC)CC)C>[CH2:34]([N:24]1[CH2:23][CH2:22][CH:21]([CH2:20][CH2:19][O:18][C:15]2[CH:16]=[CH:17][C:12]([C:9]3[N:8]=[C:7]([C:31]#[N:32])[N:6]=[C:5]4[C:10]=3[N:11]=[C:3]([CH3:2])[N:4]4[CH3:33])=[CH:13][C:14]=2[C:27]([F:29])([F:30])[F:28])[CH2:26][CH2:25]1)[CH3:35]

Participants

9

Reactant 4

HCID 177AcetaldehydeHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 117899599HCID 117899599, compound

Product 1

HCID 117899620HCID 117899620, compoundYield 62.8%

Reagents, catalysts & solvents 4

HCID 176Acetic AcidSolventHCID 6212ChloroformSolventHCID 63651,1-DichloroethaneSolventHCID 8471TriethylamineSolvent

Procedure

Triethylamine (114 μL) was added to a suspension of 8,9-dimethyl-6-{4-[2-(piperidin-4-yl)ethoxy]-3-(trifluoromethyl)phenyl}-9H-purine-2-carbonitrile monohydrochloride (128 mg) in dichloroethane (3 mL) at room temperature, and the mixture was stirred at the same temperature for 15 minutes. After the reaction mixture was ice-cooled, acetic acid (76 μL), sodium triacetoxyborohydride (113 mg), and acetaldehyde (45 μL) were added thereto, and the mixture was stirred for 1 hour under ice-cooling. After a saturated aqueous NaHCO3 solution was added to the reaction mixture, extraction thereof was performed using CHCl3, and the extract was washed with water and saturated brine. The organic layer was dried over MgSO4 and filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by basic silica gel column chromatography (CHCl3). The obtained product was washed with diisopropyl ether, and collected by filtration, whereby 6-{4-[2-(1-ethylpiperidin-4-yl)ethoxy]-3-(trifluoromethyl)phenyl}-8,9-dimethyl-9H-purine-2-carbonitrile (79 mg) was obtained as a pale yellow solid.

Workup

  1. temperaturecooled
  2. stirringthe mixture was stirred for 1 hour under ice-
  3. temperaturecooling
  4. washthe extract was washed with water and saturated brine
  5. dry with materialThe organic layer was dried over MgSO4
  6. filtrationfiltered
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. customThe residue was purified by basic silica gel column chromatography (CHCl3)
  9. washThe obtained product was washed with diisopropyl ether
  10. filtrationcollected by filtration

Sources & evidence

ORD record
ord-2f7a4e5ec1504b608401d55d807451c2
Source dataset
uspto-grants-2016_05
Patent number
US09328118B2

Reaction notes

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