Methanethiol → 7-(Methylthio)-1,8-naphthyridin-2-amine

HRID 235826Notes

Reaction equation

HRID 235826 reaction equation
[CH3:1][SH:2].[H-].[Na+].[NH2:5][C:6]1[CH:15]=[CH:14][C:13]2[C:8](=[N:9][C:10](Cl)=[CH:11][CH:12]=2)[N:7]=1.O>CN(C)C=O.C(O)C>[NH2:5][C:6]1[CH:15]=[CH:14][C:13]2[C:8](=[N:9][C:10]([S:2][CH3:1])=[CH:11][CH:12]=2)[N:7]=1

Participants

7

Reactant 4

HCID 878MethanethiolHCID 962WaterHCID 24758Sodium hydrideHCID 851997-Chloro-1,8-naphthyridin-2-amine

Product 1

HCID 221638437-(Methylthio)-1,8-naphthyridin-2-amine

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a solution, close to saturation, of methyl mercaptan in dimethylformamide (200 cc) maintained at 0° C., sodium hydride (13.3 g) in 50% strength suspension in mineral oil is added in small portions. 2-Amino-7-chloro-1,8-naphthyridine (25 g) is then added to this solution, and the mixture is heated at 100° C. for 2 hours. After being cooled, the reaction mixture is poured into water (500 cc) and extracted with methylene chloride (5×250 cc). The organic extracts are then washed with distilled water (2×200 cc), dried over magnesium sulphate and concentrated to dryness at 40° C. under reduced pressure (4 kPa). The product produced (22.9 g; m.p. 130° C.) is dissolved in boiling ethanol (150 cc). After 2 hours' cooling at 4° C., the crystallised solid is separated by filtration, washed with ethanol (10 cc) and then isopropyl ether (3×10 cc), and dried at 40° C. under reduced pressure (0.067 kPa). 2-Amino-7-methylthio-1,8-naphthyridine (9.6 g) is produced, m.p. 158° C.

Workup

  1. temperaturethe mixture is heated at 100° C. for 2 hours
  2. temperatureAfter being cooled
  3. extractionextracted with methylene chloride (5×250 cc)
  4. washThe organic extracts are then washed with distilled water (2×200 cc)
  5. dry with materialdried over magnesium sulphate
  6. concentrationconcentrated to dryness at 40° C. under reduced pressure (4 kPa)
  7. customThe product produced (22.9 g; m.p. 130° C.)
  8. dissolutionis dissolved
  9. temperatureAfter 2 hours' cooling at 4° C.
  10. customthe crystallised solid is separated by filtration
  11. washwashed with ethanol (10 cc)
  12. dry with materialisopropyl ether (3×10 cc), and dried at 40° C. under reduced pressure (0.067 kPa)

Sources & evidence

ORD record
ord-6d055f61fa2c4ee1bbf9ee1636c9ccae
Source dataset
uspto-grants-1987_02
Patent number
US04642308

Reaction notes

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