Toluene → 3,6-dimethyl-N-(2-phenylimidazo[1,2-a]pyrimidin-7-yl)picolinamide

HRID 1958315Notes

Reaction equation

HRID 1958315 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.C1(C)C=CC=CC=1.C[O:29][C:30]([C:32]1[C:37]([CH3:38])=[CH:36][CH:35]=[C:34]([CH3:39])[N:33]=1)=O>O1CCOCC1>[CH3:38][C:37]1[C:32]([C:30]([NH:15][C:13]2[CH:12]=[CH:11][N:10]3[CH:16]=[C:7]([C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)[N:8]=[C:9]3[N:14]=2)=[O:29])=[N:33][C:34]([CH3:39])=[CH:35][CH:36]=1

Participants

6

Reactant 4

HCID 1140TolueneHCID 10511234Methyl 3,6-dimethylpicolinateHCID 16682925TrimethylaluminumHCID 508783902-Phenylimidazo[1,2-A]pyrimidin-7-amine

Product 1

HCID 534667113,6-dimethyl-N-(2-phenylimidazo[1,2-a]pyrimidin-7-yl)picolinamideYield 43.7%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To a white suspension of 2-phenyl-imidazo[1,2-a]pyrimidin-7-ylamine (example 1, step 1, 80 mg, 0.38 mmole) in dioxane (3 ml) is added at RT trimethyl aluminium sol. 2M in toluene (0.8 ml, 1.52 mmole, 4 eq.). The mixture is stirred for 45 min at RT. A solution of 3,6-dimethyl-pyridine-2-carboxylic acid methyl ester (63 mg, 0.38 mmole, 1 eq.) in dioxane (0.4 ml) is then added and the light brown solution is refluxed overnight. The brown solution is loaded on 2 g silica and purified by chromatography on a 12 g RediSep silica cartridge (eluent heptane/ethyl acetate 30-70% 15 min) affording 3,6-dimethyl-N-(2-phenylimidazo[1,2-a]pyrimidin-7-yl)picolinamide (57 mg, 43.6%) as a white solid. MS (m/e)=344.2 [M+H+].

Workup

  1. temperaturethe light brown solution is refluxed overnight
  2. custompurified by chromatography on a 12 g RediSep silica cartridge (eluent heptane/ethyl acetate 30-70% 15 min)

Sources & evidence

ORD record
ord-d232d4280e7c42dd80fa86105863e6c7
Source dataset
uspto-grants-2013_04
Patent number
US08410117B2

Reaction notes

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