2-Bromopyridine → 7H-Pyrrolo[2,3-d]pyrimidine, 2-chloro-5-methyl-7-(2-pyridinyl)-

HRID 2189299Notes

Reaction equation

[Cl:1][C:2]1[N:3]=[CH:4][C:5]2[C:10]([CH3:11])=[CH:9][NH:8][C:6]=2[N:7]=1.Br[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].N[C@@H]1CCCC[C@H]1N>O1CCOCC1.C(OCC)(=O)C.[Cu]I>[Cl:1][C:2]1[N:3]=[CH:4][C:5]2[C:10]([CH3:11])=[CH:9][N:8]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=3)[C:6]=2[N:7]=1

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of 2-Chloro-5-methyl-7H-pyrrolo[2,3-d]pyrimidine (80 mg, 0.48 mmol), 2-bromopyridine (113 mg, 0.72 mmol), copper(I) iodide (9.1 mg, 0.48 mmol), K3PO4 (2.02 g, 23.84 mmol), and trans-1,2-diaminocyclohexane (5.44 mg, 0.48 mmol) in 1,4-dioxane (7 mL) is stirred at 90° C. for 1.5 hrs. After cooling to room temperature the reaction mixture is diluted with ethyl acetate and washed with brine. The organic phase is dried (anhydrous Na2SO4) and the solvent is evaporated. The crude product is purified by flash chromatography (gradient elution ethyl acetate:heptanes 0:1 to 1:4) on silicagel to afford 2-Chloro-5-methyl-7-pyridin-2-yl-7H-pyrrolo[2,3-d]pyrimidine as a white solid (55%).

Workup

temperatureAfter cooling to room temperature the reaction mixture
washwashed with brine
dry with materialThe organic phase is dried (anhydrous Na2SO4)
customthe solvent is evaporated
customThe crude product is purified by flash chromatography (gradient elution ethyl acetate:heptanes 0:1 to 1:4) on silicagel

Sources & evidence

ORD record: ord-f7257d9904444872b8367179e5c02c81
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08324225B2

Reaction notes

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