Triphenylphosphine → ((5,8-Dimethyl-[1,2,4]triazolo[1,5-a]pyrazin-2-yl)methyl)triphenylphosphonium chloride

HRID 1054926Notes

Reaction equation

HRID 1054926 reaction equation
[Cl:1][CH2:2][C:3]1[N:13]=[C:6]2[C:7]([CH3:12])=[N:8][CH:9]=[C:10]([CH3:11])[N:5]2[N:4]=1.[C:14]1([P:20]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C(#N)C>[Cl-:1].[CH3:11][C:10]1[N:5]2[N:4]=[C:3]([CH2:2][P+:20]([C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)[N:13]=[C:6]2[C:7]([CH3:12])=[N:8][CH:9]=1

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 591512352-(Chloromethyl)-5,8-dimethyl-[1,2,4]triazolo[1,5-a]pyrazine

Product 1

HCID 86665503((5,8-Dimethyl-[1,2,4]triazolo[1,5-a]pyrazin-2-yl)methyl)triphenylphosphonium chlorideYield 110.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 2-(chloromethyl)-5,8-dimethyl-[1,2,4]triazolo[1,5-a]pyrazine (prepared as described in WO2009152825) (500 mg, 2.54 mmol, Eq: 1.00) and triphenylphosphine (667 mg, 2.54 mmol, Eq: 1.00) in acetonitrile (24.9 ml) was refluxed for 18 hours under argon atmosphere. The solvent was evaporated the light pink solid was triturated with ether, the solid was filtered off, washed with ether and dried in vacuo affording (5,8-dimethyl-[1,2,4]triazolo[1,5-a]pyrazin-2-ylmethyl)-triphenyl-phosphonium chloride (1.292 g, 72.5%) as a light pink solid. MS-Cl: m/e=423 (M+H+)

Workup

  1. temperaturewas refluxed for 18 hours under argon atmosphere
  2. customThe solvent was evaporated the light pink solid
  3. customwas triturated with ether
  4. filtrationthe solid was filtered off
  5. washwashed with ether
  6. customdried in vacuo

Sources & evidence

ORD record
ord-077386b0b00747758c6247a3e03f40d5
Source dataset
uspto-grants-2016_07
Patent number
US09394311B2

Reaction notes

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