Ammonium Chloride → 4-Chloro-6-(methylsulfanyl)pyrimidine

HRID 1592242Notes

Reaction equation

HRID 1592242 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6](Cl)[N:5]=[CH:4][N:3]=1.[CH3:9][S-:10].[Na+].[Cl-].[NH4+]>C(O)C>[Cl:1][C:2]1[CH:7]=[C:6]([S:10][CH3:9])[N:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 709434,6-DichloropyrimidineHCID 4378561Sodium methanethiolate

Product 1

HCID 218130774-Chloro-6-(methylsulfanyl)pyrimidineYield 68%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

1H-NMR: 4.85 (bs, 2H), 6.29 (s, 1H), 7.21-7.39 (m, 3H), 8.64 (s, 1H) To 10 ml of an ethanol solution of 1.5 g of 4,6-dichloropyrimidine was slowly added 0.78 g of sodium thiomethoxide at 0° C., followed by stirring at 0° C. for 7 hours. A saturated aqueous ammonium chloride solution was added to the reaction mixture and concentrated under reduced pressure. The residue was extracted three times with chloroform. The chloroform layers were combined, washed with water, dried over anhydrous magnesium sulfate, and then concentrated. The residue was subjected to silica gel column chromatography to give 1.1 g of 4-chloro-6-methylthiopyrimidine.

Workup

  1. customat 0° C.
  2. concentrationconcentrated under reduced pressure
  3. extractionThe residue was extracted three times with chloroform
  4. washwashed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-d9a603d27ff244478fd439952dc0b253
Source dataset
uspto-grants-2007_11
Patent number
US07291730B2

Reaction notes

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