Piperazine → 3-Piperazin-1-ylmethyl-pyrimido[5,4-e][1,2,4]triazine-5,7-diamine

HRID 479097Notes

Reaction equation

HRID 479097 reaction equation
Cl[CH2:2][C:3]1[N:4]=[N:5][C:6]2[C:7](=[C:9]([NH2:14])[N:10]=[C:11]([NH2:13])[N:12]=2)[N:8]=1.[NH:15]1[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1>C(O)C>[N:15]1([CH2:2][C:3]2[N:4]=[N:5][C:6]3[C:7](=[C:9]([NH2:14])[N:10]=[C:11]([NH2:13])[N:12]=3)[N:8]=2)[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1

Participants

4

Reactant 2

HCID 4837PiperazineHCID 11390207HCID 11390207, compound

Product 1

HCID 121095363-Piperazin-1-ylmethyl-pyrimido[5,4-e][1,2,4]triazine-5,7-diamineYield 58%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 3-Chloromethyl-pyrimido[5,4-e][1,2,4]triazine-5,7-diamine 3 (2.00 g; 9.5 mmol) and piperazine (2.50 g; 29 mmol) in absolute ethanol was heated to 100° C. in a sealed tube for 4 h. The mixture was then allowed to cool to room temperature and evaporated. The crude product was purified by reverse phase HPLC (Rainin C18, 0% CH3CN to 30% CH3CN gradient, CH3CN/H2O, 0.1% TFA) and the bright yellow fractions containing the product were lyophilized after removal of CH3CN in vacuo to give 1.44 g of yellow colored 3-Piperazin-1-ylmethyl-pyrimido[5,4-e][1,2,4]triazine-5,7-diamine 5 as the trifluoroacetate salt.

Workup

  1. temperatureto cool to room temperature
  2. customevaporated
  3. customThe crude product was purified by reverse phase HPLC (Rainin C18, 0% CH3CN to 30% CH3CN gradient, CH3CN/H2O, 0.1% TFA)
  4. additionthe bright yellow fractions containing the product
  5. customafter removal of CH3CN in vacuo

Sources & evidence

ORD record
ord-cc7eec651525458d97a73fc51172fa12
Source dataset
uspto-grants-2003_11
Patent number
US06642381B2

Reaction notes

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