Sodium Nitrite → 4-(6-Azido-2-{2-[(pyridin-2-yl)oxy]ethoxy}pyrimidin-4-yl)morpholine
Reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[O:7][CH2:8][CH2:9][O:10][C:11]1[N:16]=[C:15]([N:17]2[CH2:22][CH2:21][O:20][CH2:19][CH2:18]2)[CH:14]=[C:13]([NH:23][NH2:24])[N:12]=1.[N:25]([O-])=O.[Na+]>CC(O)=O>[N:23]([C:13]1[N:12]=[C:11]([O:10][CH2:9][CH2:8][O:7][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=2)[N:16]=[C:15]([N:17]2[CH2:22][CH2:21][O:20][CH2:19][CH2:18]2)[CH:14]=1)=[N+:24]=[N-:25]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
As shown in Scheme I above, to a solution of 2-[2-(pyridin-2-yloxy)-ethoxy]-6-hydrazino-4-morphlinopyrimidine (4.98 g, 15.00 mmol, 1.00 equiv.) in 40 mL HOAc was added NaNO2 (1.553 g, 22.50 mmol, 1.50 equiv.) in six portions over a period of 1 hour. The reaction mixture was stirred at room temperature for 1 hour, and subjected to usual workup to yield 6-azido-2-[2-(pyridin-2-yloxy)-ethoxy]-4-morphlinopyrimidine as green viscous oil (5.0 g, 14.57 mmol, 97% yield). This oil was dissolved in 80 mL THF, and subjected to hydrogenation in the presence of 10% Pd on carbon (0.775 g of 10% Pd/C, 0.73 mmol, 0.05 equiv.) to yield 6-amino-2-[2-(pyridin-2-yloxy)-ethoxy]-4-morphlinopyrimidine as light yellow solid (4.25 g, 13.4 mmol, 89% total yield).
Sources & evidence
- ORD record
- ord-febbb88cd4ed42e58a20744c081bc0dc
- Source dataset
- uspto-grants-2006_10
- Patent number
- US07122665B2
Reaction notes
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