Sodium Hydroxide → 2-(Methanesulfonyl)amino-4-(4-fluoronaphth-1-yl)-6-isopropylpyrimidine

HRID 619300Notes

Reaction equation

HRID 619300 reaction equation
[CH3:1][S:2]([N:5](S(C)(=O)=O)[C:6]1[N:11]=[C:10]([C:12]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:15]([F:22])=[CH:14][CH:13]=2)[CH:9]=[C:8]([CH:23]([CH3:25])[CH3:24])[N:7]=1)(=[O:4])=[O:3].[OH-].[Na+]>CO>[CH3:1][S:2]([NH:5][C:6]1[N:11]=[C:10]([C:12]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:15]([F:22])=[CH:14][CH:13]=2)[CH:9]=[C:8]([CH:23]([CH3:25])[CH3:24])[N:7]=1)(=[O:3])=[O:4]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 218464132-(Bismethanesulfonyl)amino-4-(4-fluoronaphth-1-yl)-6-isopropylpyrimidine

Product 1

HCID 218464172-(Methanesulfonyl)amino-4-(4-fluoronaphth-1-yl)-6-isopropylpyrimidine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The 2-(bismethanesulfonyl)amino-4-(4-fluoronaphth-1-yl)-6-isopropylpyrimidine product from Example 10B above (0.204 g) was dissolved in methanol (5 mL) and treated at room temperature with 2.5N sodium hydroxide solution (0.2 mL). The reaction mixture was stirred at room temperature for 1 hour. The mixture was partitioned between 1N hydrochloric acid and ethyl acetate. The organic layer was dried over magnesium sulfate and evaporated to dryness and recrystallized to afford 2-(methanesulfonyl)amino-4-(4-fluoronaphth-1-yl)-6-isopropylpyrimidine as a crystalline material, m.p. 276-276.9° C. (prior decomposition at 273° C.).

Workup

  1. customThe mixture was partitioned between 1N hydrochloric acid and ethyl acetate
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. customevaporated to dryness
  4. customrecrystallized

Sources & evidence

ORD record
ord-f507c997bf714d259acd7847439253d9
Source dataset
uspto-grants-1999_09
Patent number
US05958934

Reaction notes

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