Ammonia → 6,7-Diamino-4-ethyl-2-[(4-methoxybenzyloxy)methyl]-s-triazolo[1,5-a]pyrimidin-5-one

HRID 2297596Notes

Reaction equation

HRID 2297596 reaction equation
[NH2:1][C:2]1[N:7]2[N:8]=[C:9]([CH2:11][O:12][CH2:13][C:14]3[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=3)[N:10]=[C:6]2[N:5]([CH2:22][CH3:23])[C:4](=[O:24])[C:3]=1[N:25]=O.N.C(O)C.[O-]S(S([O-])=O)=O.[Na+].[Na+]>O>[NH2:25][C:3]1[C:4](=[O:24])[N:5]([CH2:22][CH3:23])[C:6]2[N:7]([N:8]=[C:9]([CH2:11][O:12][CH2:13][C:14]3[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=3)[N:10]=2)[C:2]=1[NH2:1]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 702EthanolHCID 24489Sodium DithioniteHCID 15432856HCID 15432856, compound

Product 1

HCID 154328576,7-Diamino-4-ethyl-2-[(4-methoxybenzyloxy)methyl]-s-triazolo[1,5-a]pyrimidin-5-oneYield 83.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

At ambient temperature, 1.5 g of 7-amino-4-ethyl-2-[(4-methoxybenzyloxy)methyl]-6-nitroso-s-triazolo[1,5-a]pyrimidin-5-one are added to 64 ml of aqueous ammonia solution (25%) and 13 ml of ethanol and dissolved therein. At 30-35° C. a solution of 3.3 g of Na2S2O4 in 30 ml of water is added dropwise. The resulting mixture is stirred at ambient temperature until the reaction is complete (about 3-4 hours). After cooling in an ice bath, the crystals obtained are suction filtered and dried. 1.2 g of 6,7-diamino-4-ethyl-2-[(4-methoxybenzyloxy)methyl]-s-triazolo[1,5-a]pyrimidin-5-one are obtained, which is used in the next step without further purification.

Workup

  1. dissolutiondissolved
  2. custom(about 3-4 hours)
  3. temperatureAfter cooling in an ice bath
  4. customthe crystals obtained
  5. filtrationare suction filtered
  6. customdried

Sources & evidence

ORD record
ord-055836331d4149679ecfd9915d321d62
Source dataset
uspto-grants-2002_12
Patent number
US06492377B1

Reaction notes

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