Sodium hydride → HCID 178517328, compound

HRID 971248Notes

Reaction equation

HRID 971248 reaction equation
[H-].[Na+].CS(C[CH2:8][OH:9])(=O)=O.[Cl:10][C:11]1[C:12]([N:17]2[CH2:26][CH2:25][C:24]3[C:23]([NH:27][C:28]4[CH:33]=[CH:32][C:31]([C:34]([F:37])([F:36])[F:35])=[CH:30][CH:29]=4)=[N:22]C(S(C)(=O)=O)=[N:20][C:19]=3[CH2:18]2)=[N:13][CH:14]=[CH:15][CH:16]=1>CN(C=O)C>[F:37][C:34]([F:35])([F:36])[C:31]1[CH:32]=[CH:33][C:28]([NH:27][C:23]2[C:24]3[CH2:25][CH2:26][N:17]([C:12]4[C:11]([Cl:10])=[CH:16][CH:15]=[CH:14][N:13]=4)[CH2:18][C:19]=3[N:20]=[C:8]([OH:9])[N:22]=2)=[CH:29][CH:30]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 848342-(Methylsulfonyl)ethanolHCID 12004367HCID 12004367, compound

Product 1

HCID 178517328HCID 178517328, compoundYield 11.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Sodium hydride (40 mg, 1 mmol, 60%) was added to a solution of 2-(methansulphonyl)ethanol (124 mg, 1 mmol) in DMF (5 mL, anhydrous) and stirred at room temperature for 10 min. This mixture (0.6 mL) was added to a solution of 7-(3-chloropyridin-2-yl)-N-(4-(trifluoromethyl)phenyl)-5,6,7,8-tetrahydro-2-(methylsulfonyl)pyrido[3,4-d]pyrimidin-4-amine (50 mg, 0.1 mmol) in DMF (1 mL) and was heated in a sealed tube via microwave at 150° C. for 20 min. Solvent was removed in vacuo and the residue was purified by column chromatography to yield the product as a light brown solid (5 mg).

Workup

  1. temperaturewas heated in a sealed tube via microwave at 150° C. for 20 min
  2. customSolvent was removed in vacuo
  3. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-e1a8f2acb8814ee78c41757a37a56413
Source dataset
uspto-grants-2007_12
Patent number
US07312330B2

Reaction notes

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