Hydrochloric Acid → HCID 86686755, compound

HRID 1403121Notes

Reaction equation

HRID 1403121 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]=[C:15]([CH3:17])[CH:14]=[CH:13][C:12]=2[NH:18]C(=O)OC(C)(C)C)[CH:3]=1.Cl.C(=O)(O)[O-].[Na+].[OH-].[Na+]>O1CCOCC1>[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][CH:14]=[C:15]([CH3:17])[CH:16]=2)[CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 516892Sodium BicarbonateHCID 86686754HCID 86686754, compound

Product 1

HCID 86686755HCID 86686755, compoundYield 95.8%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

tert-Butyl (2-{[6-chloro-2-(methylsulfanyl)pyrimidin-4-yl]amino}-4-methylphenyl)carbamate (8.5 g) was dissolved in 1,4-dioxane (85 mL), and a 4 M solution (56 mL) of hydrogen chloride in 1,4-dioxane was added thereto, followed by stirring at room temperature for 8 hours. After the completion of the reaction, a saturated aqueous sodium bicarbonate solution and a 4 M aqueous sodium hydroxide solution were added thereto. The mixture was quenched, made free, and extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and the solvent was evaporated under reduced pressure to obtain N2-[6-chloro-2-(methylsulfanyl)pyrimidin-4-yl]-4-methylbenzene-1,2-diamine (6 g) as a yellow powder.

Workup

  1. customAfter the completion of the reaction
  2. customThe mixture was quenched
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-444dc7e307cc43e69679c235b6469e68
Source dataset
uspto-grants-2014_12
Patent number
US08912180B2

Reaction notes

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