Sodium Bicarbonate → HCID 86686747, compound

HRID 1403116Notes

Reaction equation

HRID 1403116 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([S:8][CH3:9])[N:5]=[C:4]([NH:10][C:11]2[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][C:12]=2[NH:18]C(=O)C)[CH:3]=1.C(=O)(O)[O-].[Na+]>C(O)C.O1CCOCC1.Cl>[Cl:1][C:2]1[N:7]=[C:6]([S:8][CH3:9])[N:5]=[C:4]([NH:10][C:11]2[C:12]([NH2:18])=[CH:13][C:14]([CH3:17])=[CH:15][CH:16]=2)[CH:3]=1

Participants

6

Reactant 2

HCID 516892Sodium BicarbonateHCID 86686748HCID 86686748, compound

Product 1

HCID 86686747HCID 86686747, compoundYield 97.9%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolventHCID 312751,4-DioxaneSolvent

Procedure

N-(2-{[6-Chloro-2-(methylsulfanyl)pyrimidin-4-yl]amino}-5-methylphenyl)acetamide (270 mg) was dissolved in a mixed solvent of ethanol (2.8 mL) and 1,4-dioxane (2.8 mL), and 6 M hydrochloric acid (9.6 mL) was added thereto, followed by heating and refluxing for 3 hours. After air-cooling to room temperature, the pH was adjusted to 6 to 7 using saturated aqueous sodium bicarbonate, followed by extraction with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and the solvent was evaporated under reduced pressure to obtain N1-[6-chloro-2-(methylsulfanyl)pyrimidin-4-yl]-4-methylbenzene-1,2-diamine (230 mg).

Workup

  1. additionwas added
  2. temperatureby heating
  3. temperaturerefluxing for 3 hours
  4. extractionfollowed by extraction with ethyl acetate
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-d752b673e3ad4b15a6ca772fc9304af5
Source dataset
uspto-grants-2014_12
Patent number
US08912180B2

Reaction notes

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