Triphenylphosphine → Chloride

HRID 2175357Notes

Reaction equation

HRID 2175357 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>[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.[Cl-:1]

Participants

5

Reactant 2

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

Product 2

HCID 312ChlorideHCID 59151223(5,8-Dimethyl-[1,2,4]triazolo[1,5-a]pyrazin-2-ylmethyl)-triphenyl-phosphonium

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 2-chloromethyl-5,8-dimethyl-[1,2,4]triazolo[1,5-a]pyrazine (1.351 g, 6.87 mmol) and triphenylphosphine (1.80 g, 6.87 mmol) in acetonitrile 150 mL was heated at reflux for 12 h. The solvents were removed in vacuo and the residue slurried in ether, filtered and dried to yield (5,8-Dimethyl-[1,2,4]triazolo[1,5-a]pyrazin-2-ylmethyl)-triphenyl-phosphonium, chloride as an off white solid (2.412 g, 74.9%). LC-MS: m/z=423.2 ([M-Cl]*), tR=0.86 minutes, method A.

Workup

  1. temperatureat reflux for 12 h
  2. customThe solvents were removed in vacuo
  3. filtrationfiltered
  4. customdried

Sources & evidence

ORD record
ord-1902a3f0ce94462490087a2f7f3517da
Source dataset
uspto-grants-2015_06
Patent number
US09062060B2

Reaction notes

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