Sodium hydride → HCID 59292302, compound

Temperature

90 °C

Into a 250 mL round bottom flask was added 3-methoxy-propanol (5.26 g, 58.4 mmol) and DMF (156 mL). Sodium hydride (60%, 4.67 g, 3 eq) was added slowly to the solution. After addition the mixture was heated to 90° C. for one hour. 2-chloro-6-amino-pyridine was added and the mixture was heated to reflux for four hours. LCMS showed conversion to product. The reaction was cooled to room temperature and solvent was removed under vacuum. The residue was partitioned between water and ethyl acetate. Organic layer was separated and the aqueous was extracted three times with ethyl acetate (3×50 mL). Organic layer dried over sodium sulfate and filtered; the solvent was removed under vacuum. The residue was dissolved with 2N HCl in MeOH and stirred for five hours at room temperature; the solvent was removed and the residue was purified by column chromatography with 20% ethyl acetate in hexanes yielding 3.12 g (45%) of the title compound as a yellow oil.

1. additionAfter addition the mixture
2. temperaturethe mixture was heated
3. temperatureto reflux for four hours
4. temperatureThe reaction was cooled to room temperature
5. customsolvent was removed under vacuum
6. customThe residue was partitioned between water and ethyl acetate
7. customOrganic layer was separated
8. extractionthe aqueous was extracted three times with ethyl acetate (3×50 mL)
9. dry with materialOrganic layer dried over sodium sulfate
10. filtrationfiltered
11. customthe solvent was removed under vacuum
12. dissolutionThe residue was dissolved with 2N HCl in MeOH
13. customthe solvent was removed
14. customthe residue was purified by column chromatography with 20% ethyl acetate in hexanes yielding 3.12 g (45%) of the title compound as a yellow oil

ORD record

ord-3069fec3f00f48b7b746b5429ec6f42e

Source dataset

uspto-grants-2012_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08148367B2