Hydrogen Sulfide → 4-Amino-2-(methylthio)-5-pyrimidinecarbothioamide

HRID 2285594Notes

Reaction equation

HRID 2285594 reaction equation
[SH2:1].[NH2:2][C:3]1[C:8]([C:9]#[N:10])=[CH:7][N:6]=[C:5]([S:11][CH3:12])[N:4]=1.C(N(CC)CC)C>N1C=CC=CC=1>[NH2:2][C:3]1[C:8]([C:9](=[S:1])[NH2:10])=[CH:7][N:6]=[C:5]([S:11][CH3:12])[N:4]=1

Participants

5

Reactant 3

HCID 402Hydrogen SulfideHCID 8471TriethylamineHCID 2957574-Amino-2-(methylsulfanyl)pyrimidine-5-carbonitrile

Product 1

HCID 128311684-Amino-2-(methylthio)-5-pyrimidinecarbothioamide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Hydrogen sulfide is passed through a suspension of 4-amino-2-methylthio-5-pyrimidinecarbonitrile (16.621 g., 0.100 mole) in a mixture of pyridine (150 ml.) and triethylamine (14.0 ml., 0.100 mole) for 2 hours. The nitrile dissolves in the course of the reaction. After ca. 1.75 hours a solid begins to separate. The mixture is poured into water (500 ml.), and the yellow solid collected by filtration washed with water, dried at 100° C., house vac. The yield of product melting at 230° C. dec. (uncorr.) is 18.93 (94.5%). This material is recrystallized from dimethylformamide-water (Darco G-60) to give yellow rods melting at 229° C. dec. (uncorr.) in a yield of 15.685 g. (78.3%).

Workup

  1. customto separate
  2. additionThe mixture is poured into water (500 ml.)
  3. filtrationthe yellow solid collected by filtration
  4. washwashed with water
  5. customdried at 100° C.
  6. customThis material is recrystallized from dimethylformamide-water (Darco G-60)
  7. customto give yellow rods melting at 229° C. dec. (uncorr.) in a yield of 15.685 g

Sources & evidence

ORD record
ord-d139e8b62fe84ee38d97c8bd0d016be8
Source dataset
uspto-grants-1982_04
Patent number
US04323681

Reaction notes

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