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Pyrrolidine → HCID 12109537, compound

HRID 479099
Notes
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Reaction equation

HRID 479099 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[CH2:19][CH2:18][CH2:17][CH2:16]1>>[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)[CH2:19][CH2:18][CH2:17][CH2:16]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

3

Reactant 2

HCID 31268PyrrolidineHCID 11390207HCID 11390207, compound

Product 1

HCID 12109537HCID 12109537, compound

Conditions

Temperature
80 °C

Procedure

A mixture of 3-Chloromethyl-pyrimido[5,4-e][1,2,4]triazine-5,7-diamine 3 (70 mg; 0.33 mmol) and 1.0 mL of pyrrolidine were heated to 80° C. in a sealed tube for 7 h. The mixture was then allowed to cool to room temperature and concentrated in vacuo. 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 50 mg of yellow colored 3-Pyrrolidin-1-ylmethyl-pyrimido[5,4-e][1,2,4]triazine-5,7-diamine as the trifluoroacetate salt.

Workup

temperature
to cool to room temperature
  • concentrationconcentrated in vacuo
  • customThe crude product was purified by reverse phase HPLC (Rainin C18, 0% CH3CN to 30% CH3CN gradient, CH3CN/H2O, 0.1% TFA)
  • additionthe bright yellow fractions containing the product
  • customafter removal of CH3CN in vacuo
  • Sources & evidence

    ORD record
    ord-f1d4da2a2e6140ee8a69aa06a5db3714
    Source dataset
    uspto-grants-2003_11
    DOI
    10.6084/m9.figshare.5104873.v1
    Patent number
    US06642381B2

    Reaction notes

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    On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes