Sodium hydride → 3-(5-Iodo-pyridin-2-yloxy)-azetidine-1-carboxylic acid pyrimidin-4-ylamide

A solution of 4-aminopyrimidine (Aldrich, 243 mg, 2.54 mmol) in anhydrous DMF (4 mL) was added via syringe to a suspension of sodium hydride (60 wt % dispersion in mineral oil, 185 mg, 4.62 mmol) in anhydrous DMF (4 mL) under a nitrogen atmosphere. The mixture was stirred for 5 min. then a solution of 3-(5-Iodo-pyridin-2-yloxy)-azetidine-1-carboxylic acid 4-nitro-phenyl ester (1.02 g, 2.31 mmol) in anhydrous DMF (6 mL) was added drop-wise and the resulting yellow coloured turbid mixture was stirred at ambient temperature for 1.5 hr. The reaction mixture was poured into sat. aqueous ammonium chloride solution (30 mL) and extracted with ethyl acetate (3×100 mL). The combined organic phases were washed with sat. aqueous sodium chloride solution (100 mL) and dried over sodium sulphate. The mixture was filtered and the filtrate solvents removed in vacuo to afford a yellow solid, which was triturated with diethyl ether, filtered and dried to afford the title compound (594 mg, 65%) as a colourless solid.

1. stirringwas stirred at ambient temperature for 1.5 hr
2. extractionextracted with ethyl acetate (3×100 mL)
3. washThe combined organic phases were washed with sat. aqueous sodium chloride solution (100 mL)
4. dry with materialdried over sodium sulphate
5. filtrationThe mixture was filtered
6. customthe filtrate solvents removed in vacuo
7. customto afford a yellow solid, which
8. customwas triturated with diethyl ether
9. filtrationfiltered
10. customdried

ORD record

ord-940d6588c47543a1aed8cef375d02c38

Source dataset

uspto-grants-2015_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09006269B2