1,8-Diazabicyclo(5.4.0)undec-7-ene → Cyclopropyl-{5-[2-(5,7-dimethyl-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)-vinyl]-1-methyl-1H-[1,2,4]triazol-3-yl}-methyl-amine

HRID 1054968Notes

Reaction equation

[CH:1]1([N:4]([CH3:13])[C:5]2[N:9]=[C:8]([CH:10]=O)[N:7]([CH3:12])[N:6]=2)[CH2:3][CH2:2]1.[Cl-].[CH3:15][C:16]1[CH:21]=[C:20]([CH3:22])[N:19]2[N:23]=[C:24]([CH2:26][P+](C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[N:25]=[C:18]2[N:17]=1.C1CCN2C(=NCCC2)CC1>O1CCCC1>[CH:1]1([N:4]([C:5]2[N:9]=[C:8]([CH:10]=[CH:26][C:24]3[N:25]=[C:18]4[N:17]=[C:16]([CH3:15])[CH:21]=[C:20]([CH3:22])[N:19]4[N:23]=3)[N:7]([CH3:12])[N:6]=2)[CH3:13])[CH2:3][CH2:2]1

Participants

Conditions

Temperature: 25 °C

Procedure

To a solution of 3-(cyclopropyl(methyl)amino)-1-methyl-1H-1,2,4-triazole-5-carbaldehyde (45 mg, 250 μmol, Eq: 1.00) in tetrahydrofuran (2.3 ml) were added ((5,7-dimethyl-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)methyl)triphenylphosphonium chloride (115 mg, 250 μmol, Eq: 1.00) and DBU (95.0 mg, 94.1 μl, 624 μmol, Eq: 2.5). The resulting mixture was stirred for 18 hours at 25° C. TLC (Hep/EtOAC 1:1/UV 254 nm) showed no starting material left and new product spot. MS showed product peak also. The crude material was applied on silicagel and purified by flash chromatography over a 20 g silicagel column using heptane/ethyl acetate 1:1 as eluent to give Cyclopropyl-{5-[2-(5,7-dimethyl-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)-vinyl]-1-methyl-1H-[1,2,4]triazol-3-yl}-methyl-amine (30 mg, 37%) as light yellow waxy solid

Workup

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custompurified by flash chromatography over a 20 g silicagel column

Sources & evidence

ORD record: ord-211e7160b25944e5ae2b249d751c8db3
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09394311B2

Reaction notes

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