Sodium Hydroxide → HCID 22257979, compound

HRID 567916Notes

Reaction equation

HRID 567916 reaction equation
O[CH:2]([C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([F:25])[CH:20]=1)[C:3]1[S:18][C:6]2[N:7]([CH2:14][CH:15]([CH3:17])[CH3:16])[C:8](=[O:13])[N:9]([CH3:12])[C:10](=[O:11])[C:5]=2[CH:4]=1.[OH-].[Na+]>FC(F)(F)C(O)=O>[F:25][C:21]1[CH:20]=[C:19]([CH2:2][C:3]2[S:18][C:6]3[N:7]([CH2:14][CH:15]([CH3:16])[CH3:17])[C:8](=[O:13])[N:9]([CH3:12])[C:10](=[O:11])[C:5]=3[CH:4]=2)[CH:24]=[CH:23][CH:22]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 22258021HCID 22258021, compound

Product 1

HCID 22257979HCID 22257979, compoundYield 9%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

To a solution of 6-(1-hydroxy-(3-fluorophenyl)methyl)-3-methyl-1-(2-methylpropyl)thieno[2,3-d]pyrimidine-2,4-(1H, 3H)-dione (Example 51) (957 mg) in trifluoroacetic acid (7 ml) was added then poured onto 10% sodium hydroxide and extracted with ethyl acetate. The organic was then poured onto 10% sodium hydroxide and extracted with ethyl acetate. The organic layer was dried over magnesium sulfate and then concentrated in vacuo to a viscous oil. The oil was purified by normal phase HPLC to give the title compound (82 mg).

Workup

  1. extractionextracted with ethyl acetate
  2. additionThe organic was then poured onto 10% sodium hydroxide
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. concentrationconcentrated in vacuo to a viscous oil
  6. customThe oil was purified by normal phase HPLC

Sources & evidence

ORD record
ord-6ff6479f98954cf0b8eb4e9ea49ed3d6
Source dataset
uspto-grants-2001_01
Patent number
US06180635B2

Reaction notes

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