Sodium hydride → HCID 135671183, compound

HRID 1384607Notes

Reaction equation

HRID 1384607 reaction equation
[H-].[Na+].[SH:3][C:4]1[CH:9]=[CH:8][N:7]=[CH:6][CH:5]=1.F[C:11]1[CH:20]=[C:19]2[C:14]([C:15](=[O:21])[NH:16][CH:17]=[N:18]2)=[CH:13][CH:12]=1>CN(C=O)C.O>[N:7]1[CH:8]=[CH:9][C:4]([S:3][C:11]2[CH:20]=[C:19]3[C:14]([C:15](=[O:21])[NH:16][CH:17]=[N:18]3)=[CH:13][CH:12]=2)=[CH:5][CH:6]=1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 1353984967-Fluoroquinazolin-4(3H)-oneHCID 178418431pyridine-4-thiol

Product 1

HCID 135671183HCID 135671183, compoundYield 21.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

Sodium hydride (3.3 g of a 50% suspension in mineral oil, 69 mmol) was added to a solution of 4-mercaptopyridine (8.12 g, 73 mmol) in DMF (100 ml) and the mixture stirred for 30 minutes. 7-Fluoro-3,4-dihydroquinazolin-4-one (1.5 g, 9 mmol) was added and the reaction heated at 100° C. for 4 hours. The mixture was allowed to cool, diluted with water and extracted with ethyl acetate. The organic extracts were washed with water and brine, dried (MgSO4) and the solvent removed by evaporation. The residue was purified by column chromatography eluting with methylene chloride/methanol (97/3) to give 7-(4-pyridylthio)-3,4-dihydroquinazolin-4-one (500 mg, 6%). 1H NMR Spectrum: (DMSOd6) 7.24(d, 2H); 7.54(dd, 1H); 7.70(d, 1H); 8.10(s, 1H); 8.14(d, 1H); 8.44(d, 2H) MS-ESI: 256 [MH]+

Workup

  1. temperatureto cool
  2. extractionextracted with ethyl acetate
  3. washThe organic extracts were washed with water and brine
  4. dry with materialdried (MgSO4)
  5. customthe solvent removed by evaporation
  6. customThe residue was purified by column chromatography
  7. washeluting with methylene chloride/methanol (97/3)

Sources & evidence

ORD record
ord-5fa0bb02fd104936ad18317e08728869
Source dataset
uspto-grants-2001_07
Patent number
US06258951B1

Reaction notes

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