1,2-Diaminocyclohexane → Methyl 4-methyl-1-(pyrimidin-2-yl)-1H-pyrrole-3-carboxylate

HRID 1792827Notes

Reaction equation

[CH3:1][O:2][C:3]([C:5]1[C:9]([CH3:10])=[CH:8][NH:7][CH:6]=1)=[O:4].P([O-])([O-])([O-])=O.[K+].[K+].[K+].NC1CCCCC1N.Br[C:28]1[N:33]=[CH:32][CH:31]=[CH:30][N:29]=1.CCCCCCCCCCCC>O1CCOCC1.O.[Cu]I>[CH3:1][O:2][C:3]([C:5]1[C:9]([CH3:10])=[CH:8][N:7]([C:28]2[N:33]=[CH:32][CH:31]=[CH:30][N:29]=2)[CH:6]=1)=[O:4]

Participants

Conditions

Temperature: 100 °C

Procedure

333.9 mg (2.4 mmol) 4-methyl-1H-pyrrole-3-carboxylic acid methyl ester, 891.5 mg (4.2 mmol) tri-potassium phosphate, 4 mg (0.02 mmol) CuI, 22 mg (0.2 mmol) 1,2-diaminocyclohexane and 317.9 mg (2 mmol) of 2-bromopyrimidine was suspended in 3 mL of dioxane. After addition of 90 μl of dodecane the mixture was heated in a sealed tube under argon for 12 h at 100° C. The mixture was cooled to room temperature and then diluted with water, followed by extraction with ethyl acetate. The organic layer was washed with water (twice), dried over anhydrous sodium sulfate. After filtration the solvent was distilled off under reduced pressure and the resulting residue was purified by a silica gel column flash chromatography (eluent: heptane/dichloromethane/methanol=25/2/1) to obtain 300 mg of 4-Methyl-1-pyrimidin-2-yl-1H-pyrrole-3-carboxylic acid methyl ester as a white solid.

Workup

temperatureThe mixture was cooled to room temperature
extractionfollowed by extraction with ethyl acetate
washThe organic layer was washed with water (twice),
dry with materialdried over anhydrous sodium sulfate
filtrationAfter filtration the solvent
distillationwas distilled off under reduced pressure
customthe resulting residue was purified by a silica gel column flash chromatography (eluent: heptane/dichloromethane/methanol=25/2/1)

Sources & evidence

ORD record: ord-c864c3cb49284f4dab9026da6cb4cf4e
Source dataset: uspto-grants-2006_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07078414B2

Reaction notes

Loading…