Triethylamine → 5-Azidomethyl-2-(trifluoromethyl)pyrimidine

To a solution of 5-(hydroxymethyl)-2-(trifluoromethyl)pyrimidine (Description 119; 580 mg, 3.26 mmol) and triethylamine (0.55 ml, 3.91 mmol) in anhydrous dichioromethane (15 ml) cooled in an ice-bath was added dropwise methanesulfonyl chloride (0.28 ml, 3.59 mmol), and the resulting mixture stirred at room temperature for 1 hour. The mixture was washed with water and sat NaCl, dried over Na2SO4, filtered and evaporated. The residue was dissolved in anhydrous N,N-dimethylformamide (15 ml), sodium azide (233 mg, 3.59 mmol) was added and the resulting mixture stirred at room temperature overnight. The mixture was poured into water (100 ml) and extracted with EtOAc (3×15 ml). The combined EtOAc layers were washed with water (2×50 ml), saturated NaCl (25 ml), dried over Na2SO4, filtered and evaporated to give the title compound (660 mg, 100%).

1. washThe mixture was washed with water
2. dry with materialdried over Na2SO4
3. filtrationfiltered
4. customevaporated
5. dissolutionThe residue was dissolved in anhydrous N,N-dimethylformamide (15 ml)
6. stirringthe resulting mixture stirred at room temperature overnight
7. extractionextracted with EtOAc (3×15 ml)
8. washThe combined EtOAc layers were washed with water (2×50 ml), saturated NaCl (25 ml)
9. dry with materialdried over Na2SO4
10. filtrationfiltered
11. customevaporated

ORD record

ord-2cb552c1a9ed462a9b417de6fe8e1ad1

Source dataset

uspto-grants-2007_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07285563B2