Sodium ethoxide → HCID 12004073, compound

HRID 971251Notes

Reaction equation

HRID 971251 reaction equation
[F:1][C:2]([F:35])([F:34])[C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]2[C:11]3[CH2:23][CH2:22][N:21]([C:24]4[C:29]([S:30]([CH3:33])(=[O:32])=[O:31])=[CH:28][CH:27]=[CH:26][N:25]=4)[CH2:20][C:12]=3[N:13]=[C:14](S(C)(=O)=O)[N:15]=2)=[CH:5][CH:4]=1.[O-:36][CH2:37][CH3:38].[Na+]>O1CCOCC1.C(O)C>[CH2:37]([O:36][C:14]1[N:15]=[C:10]([NH:9][C:6]2[CH:5]=[CH:4][C:3]([C:2]([F:1])([F:35])[F:34])=[CH:8][CH:7]=2)[C:11]2[CH2:23][CH2:22][N:21]([C:24]3[C:29]([S:30]([CH3:33])(=[O:32])=[O:31])=[CH:28][CH:27]=[CH:26][N:25]=3)[CH2:20][C:12]=2[N:13]=1)[CH3:38]

Participants

5

Reactant 2

HCID 2723922Sodium ethoxideHCID 59021558HCID 59021558, compound

Product 1

HCID 12004073HCID 12004073, compoundYield 76.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

N-(4-(Trifluoromethyl)phenyl)-5,6,7,8-tetrahydro-2-(methylsulfonyl)-7-(3-(methylsulfonyl)pyridin-2-yl)pyrido[3,4-d]pyrimidin-4-amine (150 mg, 0.27 mmol) was suspended in dioxane (5.0 mL) and ethanol (2.0 mL), sodium ethoxide (20 mg, 0.28 mmol) was added and the mixture was stirred at at 80° C. for 2 hrs. Solvent was removed and the residue was purified by flash chromatography over silica gel and then by preparative TLC to obtain the product as a white solid (102 mg).

Workup

  1. customSolvent was removed
  2. customthe residue was purified by flash chromatography over silica gel

Sources & evidence

ORD record
ord-843cf3e801124312944d08be436297a3
Source dataset
uspto-grants-2007_12
Patent number
US07312330B2

Reaction notes

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