Acetaldehyde → HCID 25230632, compound

HRID 1961725Notes

Reaction equation

HRID 1961725 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[N:10]=[C:11]([N:16]3[C:20]([CH3:21])=[CH:19][C:18]([CH3:22])=[N:17]3)[C:12]([NH2:15])=[N:13][CH:14]=2)=[CH:4][CH:3]=1.[CH:23](=O)[CH3:24].[Na].C(=O)([O-])O.[Na+]>ClC(Cl)C.ClCCl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9]2[N:10]=[C:11]([N:16]3[C:20]([CH3:21])=[CH:19][C:18]([CH3:22])=[N:17]3)[C:12]([NH:15][CH2:23][CH3:24])=[N:13][CH:14]=2)=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 177AcetaldehydeHCID 516892Sodium BicarbonateHCID 5360545SodiumHCID 25230631HCID 25230631, compound

Product 1

HCID 25230632HCID 25230632, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 63651,1-DichloroethaneSolvent

Procedure

5-(4-Chloro-phenylamino)-3-(3,5-dimethyl-pyrazol-1-yl) -pyrazine-2-amine (84 mg, 1.5 mmol) was dissolved in dichloroethane (4 mL). Acetaldehyde (83 μL, 1.5 mmol) was added and the reaction mixture was stirred for one hour at room temperature. Sodium triaceoxyborohydride (70 mg, 0.3 mmol) was added and the reaction mixture was stirred overnight at room temperature. Aqueous sodium hydrogen carbonate and dichloromethane were added. The phases were separated and the aqueous phase was extracted with dichloromethane (3×20 mL). The combined organic phases were washed with brine, dried over sodium sulphate, filtrated and concentrated in vacuo. The crude product was purified by flash chromatography (ethyl acetate/heptane as eluent) to give 5-(4-chloro-phenylamino)-3-(3,5-dimethyl-pyrazol-1-yl)-2-ethylamino-pyrazine (49 mg, 80%) as a green solid. Mp. 122-124° C. LC-ESI-HRMS of [M+H]+ shows 343.1444 Da. Calc. 343.143797 Da, dev. 1.8 ppm

Workup

  1. stirringthe reaction mixture was stirred overnight at room temperature
  2. customThe phases were separated
  3. extractionthe aqueous phase was extracted with dichloromethane (3×20 mL)
  4. washThe combined organic phases were washed with brine
  5. dry with materialdried over sodium sulphate
  6. filtrationfiltrated
  7. concentrationconcentrated in vacuo
  8. customThe crude product was purified by flash chromatography (ethyl acetate/heptane as eluent)

Sources & evidence

ORD record
ord-efeccb04059f4ce9a06ea39cb918176c
Source dataset
uspto-grants-2013_04
Patent number
US08415358B2

Reaction notes

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