Hydrogen Sulfide → 4-amino-2-methylpyrimidine-5-carbothioamide

HRID 2285593Notes

Reaction equation

HRID 2285593 reaction equation
[SH2:1].[NH2:2][C:3]1[C:8]([C:9]#[N:10])=[CH:7][N:6]=[C:5]([CH3:11])[N:4]=1.C(N(CC)CC)C.CN(C)C=O>N1C=CC=CC=1>[NH2:2][C:3]1[C:8]([C:9](=[S:1])[NH2:10])=[CH:7][N:6]=[C:5]([CH3:11])[N:4]=1

Participants

6

Reactant 4

HCID 402Hydrogen SulfideHCID 6228DimethylformamideHCID 8471TriethylamineHCID 696824-Amino-2-methylpyrimidine-5-carbonitrile

Product 1

HCID 40341764-amino-2-methylpyrimidine-5-carbothioamide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Hydrogen sulfide is passed through a mixture of 4-amino-2-methyl-5-pyrimidinecarbonitrile (6.707 g., 0.050 m.), triethylamine (7.0 ml., 0.050 m.), dimethylformamide (25 ml.) and pyridine (100 ml.) with stirring for 3 hours at ambient temperature. The mixture is poured into ice water (500 ml.) and the cream-colored solid which separates is collected by filtration, washed with water, dried at 110° C./0.1 mm. The yield of product melting at 260° C. dec. (uncorr.) is 7.663 g. (91.1%). This material is recrystallized from dimethylformamide-water (Darco G-60) affording colorless crystals melting at 264° C. dec. (uncorr.) in a yield of 5.110 g. (60.8%).

Workup

  1. filtrationthe cream-colored solid which separates is collected by filtration
  2. washwashed with water
  3. customdried at 110° C./0.1 mm
  4. customThis material is recrystallized from dimethylformamide-water (Darco G-60)

Sources & evidence

ORD record
ord-018d2a2ba4884700878692747fe17241
Source dataset
uspto-grants-1982_04
Patent number
US04323681

Reaction notes

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