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

HRID 1054954Notes

Reaction equation

HRID 1054954 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[CH:17]=[C:16]([CH3:18])[N:15]2[N:19]=[C:20]([CH2:22][P+](C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[N:21]=[C:14]2[N:13]=1.C1CCN2C(=NCCC2)CC1>O1CCCC1>[Br:1][C:2]1[N:6]=[C:5]([CH:7]=[CH:22][C:20]2[N:21]=[C:14]3[N:13]=[C:12]([CH3:11])[CH:17]=[C:16]([CH3:18])[N:15]3[N:19]=2)[N:4]([CH3:9])[N:3]=1

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 846623563-bromo-1-methyl-1H-1,2,4-triazole-5-carbaldehydeHCID 87327253((5,7-Dimethyl-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)methyl)triphenylphosphonium chloride

Product 1

HCID 1235660972-(2-(3-bromo-1-methyl-1H-1,2,4-triazol-5-yl)vinyl)-5,7-dimethyl-[1,2,4]triazolo[1,5-a]pyrimidineYield 47.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of 3-bromo-1-methyl-1H-1,2,4-triazole-5-carbaldehyde (193 mg, 1.02 mmol, Eq: 1.00), ((5,7-dimethyl-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)methyl)triphenylphosphonium chloride (466 mg, 1.02 mmol, Eq: 1.00) and DBU (387 mg, 383 μl, 2.54 mmol, Eq: 2.5) in tetrahydrofuran (12 ml) was stirred for 18 hours at 25° C. under argon atmosphere. Chromatography afforded) 2-[2-(5-bromo-2-methyl-2H-[1,2,4]triazol-3-yl)-vinyl]-5,7-dimethyl-[1,2,4]triazolo[1,5-a]pyrimidine (161 mg/47.4%) as a white solid. MS: m/z=334336 (M+H+), mp: 277.4° C.

Sources & evidence

ORD record
ord-5f8b2beac2d4441aa7bd610703aa5040
Source dataset
uspto-grants-2016_07
Patent number
US09394311B2

Reaction notes

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