Sodium Azide → HCID 86657078, compound
Reaction equation
Br[CH2:2][C:3]1[CH:4]=[CH:5][C:6]2[N:7]=[C:8]([Cl:19])[N:9]=[C:10]([N:13]3[CH2:18][CH2:17][O:16][CH2:15][CH2:14]3)[C:11]=2[N:12]=1.[N-:20]=[N+:21]=[N-:22].[Na+]>CN(C=O)C>[N:20]([CH2:2][C:3]1[CH:4]=[CH:5][C:6]2[N:7]=[C:8]([Cl:19])[N:9]=[C:10]([N:13]3[CH2:18][CH2:17][O:16][CH2:15][CH2:14]3)[C:11]=2[N:12]=1)=[N+:21]=[N-:22]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
To 4-(6-(bromomethyl)-2-chloropyrido[3,2-d]pyrimidin-4-yl)morpholine 7 (0.5 g) in DMF (11 mL) was added sodium azide (2 eq). The reaction was heated at 60° C. for 1 hour and then extracted with ethyl acetate and brine. The organic layer was dried (Mg2SO4), filtered and concentrated to afford 0.437 g of crude 4-(6-(azidomethyl)-2-chloropyrido[3,2-d]pyrimidin-4-yl)morpholine. This intermediate was then suspended in THF (4 mL), triphenylphosphine (2 eq) was added and the reaction was stirred at room temperature for 1.5 hours. Water (0.1 mL) was added to the reaction mixture which was then loaded onto a 10 g biotage isolute scx-2 cartridge then eluted with 2M ammonia in methanol then purified by flash column chromatography to yield 0.27 g (2-chloro-4-morpholinopyrido[3,2-d]pyrimidin-6-yl)methanamine.
Workup
- extractionextracted with ethyl acetate and brine
- dry with materialThe organic layer was dried (Mg2SO4)
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-460a746809e5497da71dff91396a32de
- Source dataset
- uspto-grants-2013_05
- Patent number
- US08440651B2
Reaction notes
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