Acetaldehyde → HCID 117899576, compound

HRID 522275Notes

Reaction equation

HRID 522275 reaction equation
Cl.[Cl:2][C:3]1[N:4]=[C:5]([C:16]2[CH:21]=[CH:20][C:19]([O:22][CH2:23][CH2:24][CH:25]3[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]3)=[C:18]([C:31]([F:34])([F:33])[F:32])[CH:17]=2)[C:6]2[CH:11]=[CH:10][N:9]([CH2:12][CH2:13][O:14][CH3:15])[C:7]=2[N:8]=1.[C:35](O[BH-](OC(=O)C)OC(=O)C)(=O)[CH3:36].[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>[Cl:2][C:3]1[N:4]=[C:5]([C:16]2[CH:21]=[CH:20][C:19]([O:22][CH2:23][CH2:24][CH:25]3[CH2:30][CH2:29][N:28]([CH2:35][CH3:36])[CH2:27][CH2:26]3)=[C:18]([C:31]([F:32])([F:33])[F:34])[CH:17]=2)[C:6]2[CH:11]=[CH:10][N:9]([CH2:12][CH2:13][O:14][CH3:15])[C:7]=2[N:8]=1

Participants

9

Reactant 4

HCID 177AcetaldehydeHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 117899594HCID 117899594, compound

Product 1

HCID 117899576HCID 117899576, compoundYield 99.6%

Reagents, catalysts & solvents 4

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

Procedure

Triethylamine (0.35 mL) was added to a suspension of 2-chloro-7-(2-methoxyethyl)-4-{4-[2-(piperidin-4-yl)ethoxy]-3-(trifluoromethyl)phenyl}-7H-pyrrolo[2,3-d]pyrimidine monohydrochloride (440 mg) in dichloroethane (8 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 (0.24 mL), sodium triacetoxyborohydride (359 mg), and acetaldehyde (0.14 mL) 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), whereby 2-chloro-4-{4-[2-(1-ethylpiperidin-4-yl)ethoxy]-3-(trifluoromethyl)phenyl}-7-(2-methoxyethyl)-7H-pyrrolo[2,3-d]pyrimidine (431 mg) was obtained as a colorless oil.

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)

Sources & evidence

ORD record
ord-ba4cbda9303c4d11b7d9d0b5ee8a1929
Source dataset
uspto-grants-2016_05
Patent number
US09328118B2

Reaction notes

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