Triethylsilane → HCID 22257979, compound

HRID 1611039Notes

Reaction equation

HRID 1611039 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.C([SiH](CC)CC)C.[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

5

Reactant 3

HCID 12052TriethylsilaneHCID 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-methypropyl)thieno[2,3-d]pyrimidine-2,4-(1H,3H)-dione (Example 51) (957 mg) in trifluoroacetic acid (7 ml) was added triethylsilane (4 ml) and the reaction was allowed to stir for 16 h. The mixture was then poured onto 10% sodium hydroxide and extracted with ethyl acetate. The organic layer was dried over magnesium sulfate arid 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. dry with materialThe organic layer was dried over magnesium sulfate arid
  3. concentrationthen concentrated in vacuo to a viscous oil
  4. customThe oil was purified by normal phase HPLC

Sources & evidence

ORD record
ord-1eccb53fc3f643aa865f1616550a4e91
Source dataset
uspto-grants-2006_01
Patent number
US06984644B2

Reaction notes

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