2-[(5-Fluoro-2-{[4-(hydroxymethyl)phenyl]amino}-4-pyrimidinyl)amino]-N-(1-methylethyl)benzamide → HCID 57974221, compound

HRID 1864077Notes

Reaction equation

HRID 1864077 reaction equation
[F:1][C:2]1[C:3]([NH:17][C:18]2[CH:29]=[CH:28][CH:27]=[CH:26][C:19]=2[C:20]([NH:22][CH:23]([CH3:25])[CH3:24])=[O:21])=[N:4][C:5]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][OH:16])=[CH:11][CH:10]=2)=[N:6][CH:7]=1>O=[Mn]=O.O1CCOCC1>[F:1][C:2]1[C:3]([NH:17][C:18]2[CH:29]=[CH:28][CH:27]=[CH:26][C:19]=2[C:20]([NH:22][CH:23]([CH3:25])[CH3:24])=[O:21])=[N:4][C:5]([NH:8][C:9]2[CH:10]=[CH:11][C:12]([CH:15]=[O:16])=[CH:13][CH:14]=2)=[N:6][CH:7]=1

Participants

4

Reactant 1

HCID 579742112-[(5-Fluoro-2-{[4-(hydroxymethyl)phenyl]amino}-4-pyrimidinyl)amino]-N-(1-methylethyl)benzamide

Product 1

HCID 57974221HCID 57974221, compoundYield 96.1%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 312751,4-DioxaneSolvent

Procedure

A 50-mL of round bottom flask was charged with 2-[(5-fluoro-2-{[4-(hydroxymethyl)phenyl]amino}-4-pyrimidinyl)amino]-N-(1-methylethyl)benzamide (200 mg, 0.5 mmol, 1.0 eq) and dioxane (20 mL). MnO2 (217 mg, 2.5 mmol, 5.0 eq) was added slowly to this solution. Upon completion of the addition, the reaction mixture was heated at reflux for 16 h. The reaction mixture was filtered through celite and the solvent was evaporated to produce the desired product (189 mg, 48% yield) which was found to be 82% pure by HPLC. MS: M(C21H20FN5O2)=393.42, (M+H)+=394. This crude material was used for next step without further purification.

Workup

  1. additionUpon completion of the addition
  2. temperaturethe reaction mixture was heated
  3. temperatureat reflux for 16 h
  4. filtrationThe reaction mixture was filtered through celite
  5. customthe solvent was evaporated

Sources & evidence

ORD record
ord-2706a0c8b295476b81e350159f5cb16f
Source dataset
uspto-grants-2009_12
Patent number
US07625903B2

Reaction notes

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