Water → 4-(N-methyl-hydrazino)-2-methylsulfanyl-pyrimidine-5-carboxylic acid ethyl ester

HRID 1351145Notes

Reaction equation

HRID 1351145 reaction equation
[CH3:1][NH:2][NH2:3].Cl[C:5]1[C:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:9][N:8]=[C:7]([S:16][CH3:17])[N:6]=1.O>C(O)C>[CH2:14]([O:13][C:11]([C:10]1[C:5]([N:2]([CH3:1])[NH2:3])=[N:6][C:7]([S:16][CH3:17])=[N:8][CH:9]=1)=[O:12])[CH3:15]

Participants

5

Reactant 3

HCID 962WaterHCID 6061MethylhydrazineHCID 800084-Chloro-2-(methylthio)pyrimidine-5-carboxylic acid ethyl ester

Product 1

HCID 588618224-(N-methyl-hydrazino)-2-methylsulfanyl-pyrimidine-5-carboxylic acid ethyl esterYield 70.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A solution of methyl hydrazine (4.0 g, 0.087 mol, 2 eq) in ethanol (50 mL) was slowly added to a solution of ethyl 4-chloro-2-methylthio-5-pyrimidinecarboxylate (10 g, 0.043 mol) in ethanol (50 mL) while keeping the reaction temperature below 15° C. After the addition was completed, the reaction mixture was stirred for 2 hours at the room temperature. Water (100 mL) was then added and the formed product was isolated by filtration. After drying, the product was recrystalized from a 1:1 toluene-hexane mixture to give 7.3 g (69%) of the desired 4-(N-methyl-hydrazino)-2-methylsulfanyl-pyrimidine-5-carboxylic acid ethyl ester; LC/MS (m/e)=243.1 (MH+), Rt=1.15 min.

Workup

  1. customthe reaction temperature below 15° C
  2. additionAfter the addition
  3. customthe formed product was isolated by filtration
  4. customAfter drying
  5. customthe product was recrystalized from a 1:1 toluene-hexane mixture

Sources & evidence

ORD record
ord-dfb0996e1b694f66aea3f0c032db6540
Source dataset
uspto-grants-2007_05
Patent number
US07217710B2

Reaction notes

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