Azetidine → 2-(2-(3-(azetidin-1-yl)-1-methyl-1H-1,2,4-triazol-5-yl)vinyl)-5,7-dimethyl-[1,2,4]triazolo[1,5-a]pyrimidine

HRID 1054955Notes

Reaction equation

HRID 1054955 reaction equation
Br[C:2]1[N:6]=[C:5]([CH:7]=[CH:8][C:9]2[N:19]=[C:12]3[N:13]=[C:14]([CH3:18])[CH:15]=[C:16]([CH3:17])[N:11]3[N:10]=2)[N:4]([CH3:20])[N:3]=1.[NH:21]1[CH2:24][CH2:23][CH2:22]1.C1(P(C2C=CC=CC=2)C2C3OC4C(=CC=CC=4P(C4C=CC=CC=4)C4C=CC=CC=4)C(C)(C)C=3C=CC=2)C=CC=CC=1.C1([O-])C=CC=CC=1.[Na+]>O1CCOCC1>[N:21]1([C:2]2[N:6]=[C:5]([CH:7]=[CH:8][C:9]3[N:19]=[C:12]4[N:13]=[C:14]([CH3:18])[CH:15]=[C:16]([CH3:17])[N:11]4[N:10]=3)[N:4]([CH3:20])[N:3]=2)[CH2:24][CH2:23][CH2:22]1

Participants

6

Reactant 4

HCID 10422AzetidineHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 4445035Phenolate SodiumHCID 1235660972-(2-(3-bromo-1-methyl-1H-1,2,4-triazol-5-yl)vinyl)-5,7-dimethyl-[1,2,4]triazolo[1,5-a]pyrimidine

Product 1

HCID 1235115082-(2-(3-(azetidin-1-yl)-1-methyl-1H-1,2,4-triazol-5-yl)vinyl)-5,7-dimethyl-[1,2,4]triazolo[1,5-a]pyrimidineYield 27.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 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 (59 mg, 177 μmol, Eq: 1.00) in dioxane (2.11 ml) was purged with argon, then azetidine (15.1 mg, 17.8 μl, 265 μmol, Eq: 1.5), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (8.17 mg, 14.1 μmol, Eq: 0.08), tris(dibenzylideneacetone)dipalladium chloroform complex (7.31 mg, 7.06 μmol, Eq: 0.04) and sodium phenolate (20.5 mg, 177 μmol, Eq: 1.00) were added. The vial was capped and irradiated at 140° C. for 60 minutes in the microwave oven. Chromatography afforded 2-[2-(5-azetidin-1-yl-2-methyl-2H-[1,2,4]triazol-3-yl)-vinyl]-5,7-dimethyl-[1,2,4]triazolo[1,5-a]pyrimidine (15 mg/27.4%) as a light yellow solid. MS: m/z=311.4 (M+H+).

Workup

  1. customThe vial was capped
  2. customirradiated at 140° C. for 60 minutes in the microwave oven

Sources & evidence

ORD record
ord-f9caaf3e6da749daaf52fe85da19b6db
Source dataset
uspto-grants-2016_07
Patent number
US09394311B2

Reaction notes

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