6,7-diamino-2-(4-tert-butylphenyl)-5H-[1,3,4]thiadiazolo[3,2-a]pyrimidin-5-one → HCID 178440782, compound

HRID 1906525Notes

Reaction equation

HRID 1906525 reaction equation
[NH2:1][C:2]1[C:7](=[O:8])[N:6]2[N:9]=[C:10]([C:12]3[CH:17]=[CH:16][C:15]([C:18]([CH3:21])([CH3:20])[CH3:19])=[CH:14][CH:13]=3)[S:11][C:5]2=[N:4][C:3]=1[NH2:22].[N:23]([O-])=O.[Na+]>Cl.O>[C:18]([C:15]1[CH:14]=[CH:13][C:12]([C:10]2[S:11][C:5]3=[N:4][C:3]4[N:22]=[N:23][NH:1][C:2]=4[C:7](=[O:8])[N:6]3[N:9]=2)=[CH:17][CH:16]=1)([CH3:19])([CH3:21])[CH3:20]

Participants

5

Reactant 2

HCID 135918366,7-diamino-2-(4-tert-butylphenyl)-5H-[1,3,4]thiadiazolo[3,2-a]pyrimidin-5-oneHCID 23668193Sodium Nitrite

Product 1

HCID 178440782HCID 178440782, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent2×

Procedure

1.0 of 6,7-diamino-2-(4-tert-butylphenyl)-5H-[1,3,4]thiadiazolo[3,2-a]pyrimidin-5-one was suspended in a mixture of 20 ml of concentrated hydrochloric acid and 20 ml of water, and 2 ml of an aqueous solution containing 0.70 g of sodium nitrite was added dropwise thereto while cooling below 5° C. and stirring. The mixture was stirred at that temperature for 1.5 hours and then diluted with water. The resulting precipitate was filtered and recrystallized from chloroform-ethanol to obtain 0.88 g of the titled compound as pale yellow prisms. Melting Point: 293°-296° C. (decomposition).

Workup

  1. additionwas added dropwise
  2. temperaturewhile cooling below 5° C.
  3. stirringThe mixture was stirred at that temperature for 1.5 hours
  4. filtrationThe resulting precipitate was filtered
  5. customrecrystallized from chloroform-ethanol

Sources & evidence

ORD record
ord-92e6b98e19e744dcaaa1f2dfd2e386ac
Source dataset
uspto-grants-1987_03
Patent number
US04652646

Reaction notes

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