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

HRID 1993593Notes

Reaction equation

[C:1]([O:5][C:6](=[O:22])[NH:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][C:15]2[CH:20]=[C:19](Cl)[N:18]=[CH:17][N:16]=2)=[CH:10][CH:9]=1)([CH3:4])([CH3:3])[CH3:2].[N-:23]=[N+:24]=[N-:25].[Na+]>CN(C=O)C>[C:1]([O:5][C:6](=[O:22])[NH:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][C:15]2[CH:20]=[C:19]([N:23]=[N+:24]=[N-:25])[N:18]=[CH:17][N:16]=2)=[CH:10][CH:9]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 80 °C

Procedure

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).

Workup

temperatureto cool to rt
concentrationconcentrated in vacuo
additionThe residue is diluted with EtOAc (25 mL) and H2O (66 mL)
customThe layers are separated
extractionthe aqueous layer is extracted with EtOAc (2×40 mL and 2×50 mL)
dry with materialThe organic phase is dried (Na2SO4)
filtrationfiltered
concentrationconcentrated
customThe residue is purified by silica gel (80 g) column chromatography CH2Cl2/Et2O, 90/10)

Sources & evidence

ORD record: ord-da02df0a76364e4c9172b3bbb07f80b0
Source dataset: uspto-grants-2010_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07652022B2

Reaction notes

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