Trimethylaluminum → 5-Bromo-3-methyl-pyridine-2-carboxylic acid (2-phenyl-imidazo[1,2-a]pyrimidin-7-yl)-amide

HRID 1958316Notes

Reaction equation

HRID 1958316 reaction equation
[C:1]1([C:7]2[N:8]=[C:9]3[N:14]=[C:13]([NH2:15])[CH:12]=[CH:11][N:10]3[CH:16]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C[Al](C)C.[Br:21][C:22]1[CH:23]=[C:24]([CH3:32])[C:25]([C:28](OC)=[O:29])=[N:26][CH:27]=1>O1CCOCC1>[C:1]1([C:7]2[N:8]=[C:9]3[N:14]=[C:13]([NH:15][C:28]([C:25]4[C:24]([CH3:32])=[CH:23][C:22]([Br:21])=[CH:27][N:26]=4)=[O:29])[CH:12]=[CH:11][N:10]3[CH:16]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 16682925TrimethylaluminumHCID 45789787Methyl 5-bromo-3-methylpicolinateHCID 508783902-Phenylimidazo[1,2-A]pyrimidin-7-amine

Product 1

HCID 673841125-Bromo-3-methyl-pyridine-2-carboxylic acid (2-phenyl-imidazo[1,2-a]pyrimidin-7-yl)-amideYield 54%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To an argon purged solution of 2-phenylimidazo[1,2-a]pyrimidin-7-amine (example 1, step 1, 80 mg, 0.381 mmol) in dioxane (5 ml) was added trimethyl aluminum solution (0.571 ml, 1.14 mmol, 3 eq). The resulting solution was stirred for 1 hour at RT. Then methyl 5-bromo-3-methylpicolinate (88 mg, 0.381 mmol) was added and the mixture was heated to reflux and stirred for 18 hours. The title compound (84 mg, 54%) was isolated from the crude product by flash chromatography on a 20 g SiO2 column using dichloromethane/methanol 0-10% as eluent. MS (m/e)=408.2 [M+H+].

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux
  3. stirringstirred for 18 hours

Sources & evidence

ORD record
ord-8dda78781cae4b1ba2ffffa5fd5e096f
Source dataset
uspto-grants-2013_04
Patent number
US08410117B2

Reaction notes

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