Sodium Azide → [4-(6-Azido-pyrimidin-4-ylmethyl)-phenyl]-carbamic acid tert-butyl ester

Participants

Reaction Conditions

Reaction Steps

A suspension of [4-(6-chloro-pyrimidin-4-ylmethyl)-phenyl]-carbamic acid tert-butyl ester (see Example 117) (1.1 g, 3.44 mmol) and sodium azide (0.31 g, 4.81 mmol, 1.4 equiv) in DMF (13 mL) is heated to 80° C. for 2.5 h. The reaction mixture is allowed to cool to rt and concentrated in vacuo. The residue is diluted with EtOAc (25 mL) and H2O (66 mL). The layers are separated and the aqueous layer is extracted with EtOAc (2×40 mL and 2×50 mL). The organic phase is dried (Na2SO4), filtered and concentrated. The residue is purified by silica gel (80 g) column chromatography CH2Cl2/Et2O, 90/10). The title compound is obtained as a white solid: ES-MS: 327.0 [M+H]+; single peak at tR=7.42 min (System 2); Rf=0.26 (CH2Cl2/Et2O, 90/10).

Provenance & Evidence