Sodium Carbonate → HCID 89810919, compound

Temperature

70 °C

A stirred suspension of 4-chloro-5-iodo-7-methyl-7H-pyrrolo[2,3-d]pyrimidine (3.31 g, 11.3 mmol), tetramethyl-2-phenyl-1,3,2-dioxaborolane (2.76 g, 13.53 mmol) and sodium carbonate (3.59 g, 33.8 mmol) in 1,4-dioxane (90 ml) and water (18.0 ml) was degassed by bubbling N2 through it for 10 min. 1,1′-Bis(diphenylphosphino)ferrocenedichloro palladium(II) dichloromethane complex (0.921 g, 1.13 mmol) was then added and the reaction mixture degassed with N2 again for 10 min before heating at 70° C. for 2 h. The solvent was removed in vacuo and the residue partitioned between saturated sodium hydrogen carbonate (90 ml) and dichloromethane (90 ml). The layers were separated and the aqueous phase extracted with dichloromethane (3×45 ml). The combined organic phases were dried (phase separator cartridge) and concentrated in vacuo. The resulting residue was purified by silica gel chromatography (gradient 0-50% ethyl acetate in cyclohexane) to afford the title compound (1.32 g, 48%). LCMS RT=1.26 min, [M(35Cl)+H]+=244.1, [M(37Cl)+H]+=246.1.

1. customwas degassed
2. customby bubbling N2 through it for 10 min
3. addition1,1′-Bis(diphenylphosphino)ferrocenedichloro palladium(II) dichloromethane complex (0.921 g, 1.13 mmol) was then added
4. customthe reaction mixture degassed with N2 again for 10 min
5. customThe solvent was removed in vacuo
6. customthe residue partitioned between saturated sodium hydrogen carbonate (90 ml) and dichloromethane (90 ml)
7. customThe layers were separated
8. extractionthe aqueous phase extracted with dichloromethane (3×45 ml)
9. customThe combined organic phases were dried (phase separator cartridge)
10. concentrationconcentrated in vacuo
11. customThe resulting residue was purified by silica gel chromatography (gradient 0-50% ethyl acetate in cyclohexane)

ORD record

ord-d0a6e2d344364f189605c7fce8719aaf

Source dataset

uspto-grants-2015_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09156853B2