Sodium hydride → HCID 57677077, compound

HRID 491263Notes

Reaction equation

HRID 491263 reaction equation
[Cl:1][C:2]1[C:10]2[C:9]([NH:11][CH2:12][CH2:13][C:14]3[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=3)=[N:8][CH:7]=[N:6][C:5]=2[S:4][CH:3]=1.[C:21]([C:25]1[O:29]C(=O)[N:27]([C:31]2[CH:36]=[CH:35][CH:34]=[C:33](F)[N:32]=2)[N:26]=1)([CH3:24])([CH3:23])[CH3:22].[H-].[Na+]>CN(C=O)C>[Cl:1][C:2]1[C:10]2[C:9]([NH:11][CH2:12][CH2:13][C:14]3[CH:19]=[CH:18][C:17]([O:20][C:33]4[N:32]=[C:31]([NH:27][NH:26][C:25](=[O:29])[C:21]([CH3:23])([CH3:22])[CH3:24])[CH:36]=[CH:35][CH:34]=4)=[CH:16][CH:15]=3)=[N:8][CH:7]=[N:6][C:5]=2[S:4][CH:3]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 67309598HCID 67309598, compoundHCID 68856325HCID 68856325, compound

Product 1

HCID 57677077HCID 57677077, compoundYield 6.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 4-{2-[(5-chlorothieno[2,3-d]pyrimidin-4-yl)amino]ethyl}phenol (0.152 g, 0.5 mmol) and 5-(tert-butyl)-3-(6-fluoropyridin-2-yl)-3H-[1,3,4]oxadiazol-2-one (0.119 g, 0.5 mmol) in anhydrous DMF (4 mL) was added 60 percent sodium hydride in mineral oil (30 mg, 0.75 mmol) portionwise. The mixture was then stirred at 100° C. overnight. After cooling the reaction was quenched with methanol. The solvent was removed in vacuo and the residue was triturated in CH2Cl2 and water. The organic phase was separated, dried over anhydrous Na2SO4, filtered, concentrated, and purified on preparative HPLC to give the decarboxylated product as a brownish foam, 16 mg, 0.03 mmol, 6.5 percent yield.

Workup

  1. temperatureAfter cooling the reaction
  2. customwas quenched with methanol
  3. customThe solvent was removed in vacuo
  4. customthe residue was triturated in CH2Cl2
  5. customThe organic phase was separated
  6. dry with materialdried over anhydrous Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. custompurified on preparative HPLC

Sources & evidence

ORD record
ord-360676f7054c4803b2b5b0b227ab094f
Source dataset
uspto-grants-2009_05
Patent number
US07531482B2

Reaction notes

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