Sodium hydride → 2-(Bromomethyl)-4-methylpyridine

A stirred solution of the 7-(1-(2-(trimethylsilyl)ethoxymethyl)-1H-pyrazol-5-yl)-1H-[1,2,3]triazolo[4,5-d]pyrimidine-5-amine (330 mg, 1 mmol) in dry DMF (5 mL) was treated with NaH (40 mg, 60% in oil, 1 mmol), stirred for 15 min, treated with tert-butyl N-(3-(bromomethyl)benzyl)carbamate (300 mg, 1 mmol) and stirred for 1 h. The mixture was partitioned between EtOAc (20 mL) and H2O (20 mL), the organic phase was dried (MgSO4), concentrated in vacuo and purified by chromatography [SiO2; iso-hexane:EtOAc (1:1)]. The resulting yellow syrup was dissolved in MeOH (3 mL), treated with HCl (2 mL, 4-M in dioxane), stirred for 17 h and the resulting solid filtered to give the title compound (258 mg, 80%) as a cream solid.

1. stirringstirred for 1 h
2. customThe mixture was partitioned between EtOAc (20 mL) and H2O (20 mL)
3. dry with materialthe organic phase was dried (MgSO4)
4. concentrationconcentrated in vacuo
5. custompurified by chromatography [SiO2; iso-hexane:EtOAc (1:1)]
6. dissolutionThe resulting yellow syrup was dissolved in MeOH (3 mL)
7. additiontreated with HCl (2 mL, 4-M in dioxane)
8. stirringstirred for 17 h
9. filtrationthe resulting solid filtered

ORD record

ord-92988dcdd1664cc5b3f4aebea4702f8d

Source dataset

uspto-grants-2006_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07141575B2