Sodium hydride → HCID 86640996, compound

HRID 1876010Notes

Reaction equation

HRID 1876010 reaction equation
[F:1][C:2]1[C:7]([C:8]2[N:13]=[CH:12][N:11]=[C:10]([NH2:14])[CH:9]=2)=[CH:6][CH:5]=[CH:4][N:3]=1.[H-].[Na+].[C:17](N1C=CC=CC1=O)(N1C=CC=CC1=O)=[S:18]>CN(C=O)C>[F:1][C:2]1[C:7]([C:8]2[CH:9]=[C:10]([N:14]=[C:17]=[S:18])[N:11]=[CH:12][N:13]=2)=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 8531621,1'-Thiocarbonyldi-2(1H)-pyridoneHCID 59286686HCID 59286686, compound

Product 1

HCID 86640996HCID 86640996, compoundYield 36.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 6-(2-fluoropyridin-3-yl)pyrimidin-4-amine (0.3 g, 1.577 mmol) in DMF was added NaH (0.126 g, 3.15 mmol). Stirring was continued for 1.5 h and 1,1′-thiocarbonyldipyridin-2(1H)-one (0.366 g, 1.577 mmol) was added. The mixture was stirred at rt for 2 h and purified on silica gel using 10-15% ethyl acetate in hexanes to give an orange solid (0.133 g, 0.573 mmol, 36%). MS (LC/MS) R.T.=2.48; [M+H]+=233.08.

Workup

  1. stirringThe mixture was stirred at rt for 2 h
  2. custompurified on silica gel using 10-15% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-98ea8dcb0eea4aea84555b1a82e1fa98
Source dataset
uspto-grants-2012_11
Patent number
US08309577B2

Reaction notes

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