Methanethiol → 2-Methylthio-4-sec.butylamino-5-nitro-6-methylpyrimidine

HRID 597467Notes

Reaction equation

HRID 597467 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][CH:9]([CH2:11][CH3:12])[CH3:10])[C:5]([N+:13]([O-:15])=[O:14])=[C:4]([CH3:16])[N:3]=1.[CH3:17][SH:18].[H-].[Na+]>C(N(CC)CC)C>[CH3:17][S:18][C:2]1[N:7]=[C:6]([NH:8][CH:9]([CH2:11][CH3:12])[CH3:10])[C:5]([N+:13]([O-:15])=[O:14])=[C:4]([CH3:16])[N:3]=1

Participants

5

Reactant 3

HCID 878MethanethiolHCID 24758Sodium hydrideHCID 18801449HCID 18801449, compound

Product 1

HCID 214450992-Methylthio-4-sec.butylamino-5-nitro-6-methylpyrimidineYield 91.5%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

12.2 g of 2-chloro-4-sec. butylamino-5-nitro-6-methylpyrimidine (0.05 mole) are dissolved in 200 ml of alcohol and 10 ml of triethylamine are added to this solution. The reaction mixture is heated to reflux temperature and then 4.5 g of methylmercaptan (0.094 mole) are passed in. Subsequently 1.2 g of sodium hydride (0.05 mole) are added at 70° C and the mixture is refluxed for 1 hour. After the reaction mixture has cooled, the sodium chloride precipitate is filtered off with suction and the filtrate is evaporated to yield 11.7 g of 2-methylthio-4-sec.butylamino-5-nitro-6-methylpyrimidine of m.p. 37°-41° C (= 91.5% yield). On recrystallisation from petroleum ether, the melting point of the product rises to 48°-50° C.

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureto reflux temperature
  3. temperaturethe mixture is refluxed for 1 hour
  4. temperatureAfter the reaction mixture has cooled
  5. filtrationthe sodium chloride precipitate is filtered off with suction
  6. customthe filtrate is evaporated

Sources & evidence

ORD record
ord-2ded226b2dbb4842a1687470fcbe7f6a
Source dataset
uspto-grants-1977_03
Patent number
US04014677

Reaction notes

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