1,8-Diazabicyclo(5.4.0)undec-7-ene → (E)-2-(2-(3-bromo-1-methyl-1H-1,2,4-triazol-5-yl)vinyl)-5,8-dimethyl-[1,2,4]triazolo[1,5-c]pyrimidine

HRID 1055007Notes

Reaction equation

[Br:1][C:2]1[N:6]=[C:5]([CH:7]=O)[N:4]([CH3:9])[N:3]=1.[Cl-].[CH3:11][C:12]1[N:17]2[N:18]=[C:19]([CH2:21][P+](C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[N:20]=[C:16]2[C:15]([CH3:41])=[CH:14][N:13]=1.C1CCN2C(=NCCC2)CC1>O1CCCC1>[Br:1][C:2]1[N:6]=[C:5](/[CH:7]=[CH:21]/[C:19]2[N:20]=[C:16]3[N:17]([C:12]([CH3:11])=[N:13][CH:14]=[C:15]3[CH3:41])[N:18]=2)[N:4]([CH3:9])[N:3]=1

Participants

Conditions

Temperature: 25 °C

Procedure

To a solution of 3-bromo-1-methyl-1H-1,2,4-triazole-5-carbaldehyde (120 mg, 632 μmol, Eq: 1.00) in tetrahydrofuran (25 ml) were added ((5,8-dimethyl-[1,2,4]triazolo[1,5-c]pyrimidin-2-yl)methyl)triphenylphosphonium chloride (290 mg, 632 μmol, Eq: 1.00) (prepared as described in WO2011150156, pp 123-125, Expl. 24 g) and DBU (106 mg, 105 μl, 695 μmol, Eq: 1.1). The resulting solution was stirred for 18 hours at 25° C. The crude material was applied on silica gel and purified by flash chromatography over a 20 g silica gel column using ethyl acetate methanol 0-10% as eluent affording 2-[(E)-2-(5-bromo-2-methyl-2H-[1,2,4]triazol-3-yl)-vinyl]-5,8-dimethyl-[1,2,4]triazolo[1,5-c]pyrimidine (154 mg, 73%) as a white solid. MS: m/z=336.63537 (M+H+)

Workup

customprepared
custompurified by flash chromatography over a 20 g silica gel column

Sources & evidence

ORD record: ord-681c992dbb7e4a9b9e497c35d2c1dfd1
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09394311B2

Reaction notes

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