1,8-Diazabicyclo(5.4.0)undec-7-ene → 2-(2-(1-ethyl-3-(pyrrolidin-1-yl)-1H-1,2,4-triazol-5-yl)vinyl)-5,8-dimethyl-[1,2,4]triazolo[1,5-a]pyrazine

HRID 1054927Notes

Reaction equation

[Cl-].[CH3:2][C:3]1[N:8]2[N:9]=[C:10]([CH2:12][P+](C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[N:11]=[C:7]2[C:6]([CH3:32])=[N:5][CH:4]=1.[CH2:33]([N:35]1[C:39]([CH:40]=O)=[N:38][C:37]([N:42]2[CH2:46][CH2:45][CH2:44][CH2:43]2)=[N:36]1)[CH3:34].N12CCCN=C1CCCCC2>O1CCCC1>[CH2:33]([N:35]1[C:39]([CH:40]=[CH:12][C:10]2[N:11]=[C:7]3[C:6]([CH3:32])=[N:5][CH:4]=[C:3]([CH3:2])[N:8]3[N:9]=2)=[N:38][C:37]([N:42]2[CH2:46][CH2:45][CH2:44][CH2:43]2)=[N:36]1)[CH3:34]

Participants

Conditions

Temperature: 25 °C

Procedure

A mixture of ((5,8-dimethyl-[1,2,4]triazolo[1,5-a]pyrazin-2-yl)methyl)triphenylphosphonium chloride (125 mg, 272 μmol, Eq: 1.00), 1-ethyl-3-(pyrrolidin-1-yl)-1H-1,2,4-triazole-5-carbaldehyde (52.9 mg, 272 μmol, Eq: 1.00) and 1,8-diazabicyclo[5.4.0]undec-7-ene (104 mg, 103 μl, 681 μmol, Eq: 2.5) in tetrahydrofuran (6 ml) was stirred for 18 hours at 25° C. under nitrogen atmosphere. The crude material was applied on silicagel and purified by flash chromatography over a 50 g silicagel column using ethyl acetate methanol 0-10% as eluent affording 2-[2-(2-ethyl-5-pyrrolidin-1-yl-2H-[1,2,4]triazol-3-yl)-vinyl]-5,8-dimethyl-[1,2,4]triazolo[1,5-a]pyrazine (37 mg/40.1%) as a bright yellow viscous oil. MS: m/e=339.5 (M+H+)

Workup

custompurified by flash chromatography over a 50 g silicagel column

Sources & evidence

ORD record: ord-22fc7ff1f5d74ab5b26c459554d38bea
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09394311B2

Reaction notes

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