Water → HCID 18460825, compound

HRID 2303307Notes

Reaction equation

HRID 2303307 reaction equation
Cl.O1CCOCC1.[C:8]([C:11]1[C:12]([NH:29][C:30]2[CH:35]=[CH:34][CH:33]=[C:32]([CH3:36])[CH:31]=2)=[N:13][C:14]([NH:17][C:18]2[CH:28]=[CH:27][C:21]([CH2:22][NH:23]C(=O)O)=[CH:20][CH:19]=2)=[N:15][CH:16]=1)(=[O:10])[NH2:9].O>C(OCC)(=O)C>[NH2:23][CH2:22][C:21]1[CH:20]=[CH:19][C:18]([NH:17][C:14]2[N:13]=[C:12]([NH:29][C:30]3[CH:35]=[CH:34][CH:33]=[C:32]([CH3:36])[CH:31]=3)[C:11]([C:8]([NH2:9])=[O:10])=[CH:16][N:15]=2)=[CH:28][CH:27]=1

Participants

5

Reactant 3

HCID 962WaterHCID 18460846HCID 18460846, compoundHCID 204431481,4-Dioxane hydrochloride

Product 1

HCID 18460825HCID 18460825, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A 4 ml portion of 4 M hydrochloric acid-dioxane solution was added to 183 mg of tert-butyl ester of {4-[5-carbamoyl-4-(3-methylanilino)pyrimidin-2-ylamino]benzyl}carbamic acid, followed by stirring at room temperature for 16 hours. Water and ethyl acetate were added to the reaction mixture, the thus formed insoluble matter was removed by filtration and the filtrate was alkalified by adding 1 M sodium hydroxide aqueous solution. After extraction with ethyl acetate, the organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The residue concentrated under a reduced pressure was recrystallized from a mixed solvent of ethyl acetate and n-hexane, thereby obtaining 44 mg of 2-(4-aminomethylanilino)-4-(3-methylanilino)pyrimidine-5-carboxamide (light yellow crystals).

Workup

  1. customthe thus formed insoluble matter was removed by filtration
  2. additionby adding 1 M sodium hydroxide aqueous solution
  3. extractionAfter extraction with ethyl acetate
  4. washthe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationThe residue concentrated under a reduced pressure
  7. customwas recrystallized from a mixed solvent of ethyl acetate and n-hexane

Sources & evidence

ORD record
ord-50254f8cbf1e490294426cd21fcf55e3
Source dataset
uspto-grants-2002_08
Patent number
US06432963B1

Reaction notes

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