Acetic Acid → 6,7-diamino-2-(4-tert-butylphenyl)-5H-[1,3,4]thiadiazolo[3,2-a]pyrimidin-5-one

HRID 1906530Notes

Reaction equation

HRID 1906530 reaction equation
[NH2:1][C:2]1[N:3]=[C:4]2[S:14][C:13]([C:15]3[CH:20]=[CH:19][C:18]([C:21]([CH3:24])([CH3:23])[CH3:22])=[CH:17][CH:16]=3)=[N:12][N:5]2[C:6](=[O:11])[C:7]=1[N+:8]([O-])=O.C(O)(=O)C>CN(C)C=O.[C].[Pd]>[NH2:8][C:7]1[C:6](=[O:11])[N:5]2[N:12]=[C:13]([C:15]3[CH:16]=[CH:17][C:18]([C:21]([CH3:23])([CH3:22])[CH3:24])=[CH:19][CH:20]=3)[S:14][C:4]2=[N:3][C:2]=1[NH2:1]

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 135918357-amino-2-(4-tert-butylphenyl)-6-nitro-5H-[1,3,4]thiadiazolo[3,2-a]pyrimidin-5-one

Product 1

HCID 135918366,7-diamino-2-(4-tert-butylphenyl)-5H-[1,3,4]thiadiazolo[3,2-a]pyrimidin-5-oneYield 79.6%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

2.75 g of 7-amino-2-(4-tert-butylphenyl)-6-nitro-5H-[1,3,4] thiadiazolo[3,2-a]pyrimidin-5-one was dissolved in 200 ml of warmed dimethylformamide, and 20 ml of acetic acid and 2.0 g of 5% palladium-carbon were added to the solution. Catalytic reduction was carried out at a temperature of 40° to 60° C. After the calculated amount of hydrogen was absorbed, the catalyst was removed by filtration while hot, and the filtrate was concentrated under reduced pressure. The precipitate formed was separated by filtration to obtain 2.0 g of 6,7-diamino-2-(4-tert-butylphenyl)-5H-[1,3,4]thiadiazolo[3,2-a]pyrimidin-5-one as yellow needles.

Workup

  1. customwas carried out at a temperature of 40° to 60° C
  2. customAfter the calculated amount of hydrogen was absorbed
  3. customthe catalyst was removed by filtration while hot, and the filtrate
  4. concentrationwas concentrated under reduced pressure
  5. customThe precipitate formed
  6. customwas separated by filtration

Sources & evidence

ORD record
ord-141518d4447f4496bf76b1a93cd84951
Source dataset
uspto-grants-1987_03
Patent number
US04652646

Reaction notes

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