Sodium hydride → HCID 25059433, compound

HRID 2244050Notes

Reaction equation

HRID 2244050 reaction equation
F[C:2]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].Cl.[C:12](N)(=[NH:14])[CH3:13].[H-].[Na+].C([O-])(O)=O.[Na+].CC([N:26](C)C)=O>>[F:10][C:8]1[CH:9]=[C:2]2[C:3]([C:4]([NH2:26])=[N:5][C:12]([CH3:13])=[N:14]2)=[CH:6][CH:7]=1

Participants

6

Reactant 5

HCID 24758Sodium hydrideHCID 31374DimethylacetamideHCID 67170Acetamidine monohydrochlorideHCID 775452,4-DifluorobenzonitrileHCID 516892Sodium Bicarbonate

Product 1

HCID 25059433HCID 25059433, compoundYield 33%

Conditions

Temperature
150 °C

Procedure

A mixture of 2,4-Difluorobenzonitrile (1.1 g, 1 eq), acetamidine hydrochloride (2.8 g, 3.78 eq) and sodium hydride (1.52 g, 8 eq) in dimethylacetamide (50 mL) is stirred at 150° C. for overnight. Then the reaction mixture is poured into sat'd NaHCO3 aq. solution (300 mL), extracted by EtOAc (3×200 mL), the combined organic layers dried over Na2SO4, filtered, concentrated to give a crude product. Purification of that by flash column chromatography yields 7-Fluoro-2-methyl-quinazolin-4-ylamine (0.46 g, 33% yield). LC/MS m/z=178 [M+H]+.

Workup

  1. extractionextracted by EtOAc (3×200 mL)
  2. dry with materialthe combined organic layers dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto give a crude product
  6. customPurification of that by flash column chromatography

Sources & evidence

ORD record
ord-468bb75e03174cf796b80f3389467320
Source dataset
uspto-grants-2010_03
Patent number
US07678803B2

Reaction notes

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