Hydrogen Sulfide → 4,6-Bis(1,1-dimethylethyl)-5-hydroxy-2-pyrimidine carbothioamide

HRID 1707981Notes

Reaction equation

HRID 1707981 reaction equation
[SH2:1].[CH3:2][C:3]([C:6]1[C:11]([OH:12])=[C:10]([C:13]([CH3:16])([CH3:15])[CH3:14])[N:9]=[C:8]([C:17]#[N:18])[N:7]=1)([CH3:5])[CH3:4].C(N(CC)CC)C>N1C=CC=CC=1>[CH3:5][C:3]([C:6]1[C:11]([OH:12])=[C:10]([C:13]([CH3:16])([CH3:15])[CH3:14])[N:9]=[C:8]([C:17](=[S:1])[NH2:18])[N:7]=1)([CH3:2])[CH3:4]

Participants

5

Reactant 3

HCID 402Hydrogen SulfideHCID 8471TriethylamineHCID 152948974,6-Bis (1,1-dimethylethyl)-5-hydroxy-2-pyrimidine carbonitrile

Product 1

HCID 1360931934,6-Bis(1,1-dimethylethyl)-5-hydroxy-2-pyrimidine carbothioamideYield 58%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Hydrogen sulfide is bubbled through a solution of 4,6-bis (1,1-dimethylethyl)-5-hydroxy-2-pyrimidine carbonitrile (4.5 g, 19.3 mmol) and triethylamine (4.3 g, 42.4 mmol) in pyridine (20 nil) at room temperature for 6 hours. The reaction mixture is stirred at room temperature overnight. The solvent is evaporated under vacuum and the residue is recrystallized from ether/hexane to give pure 4,6-bis (1,1-dimethylethyl)-5-hydroxy-2-pyrimidine carbothioamide (3.0 g, 58%); mp 169°-171° C.

Workup

  1. customThe solvent is evaporated under vacuum
  2. customthe residue is recrystallized from ether/hexane

Sources & evidence

ORD record
ord-3a72580b00e6430a9ac477618631479c
Source dataset
uspto-grants-1994_10
Patent number
US05356898

Reaction notes

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