Hydrochloric Acid → (9aR)-8-(2-chloro-5-fluoro-6-hydrazino-4-pyrimidinyl)octahydropyrazino[2,1-c][1,4]oxazine
Reaction equation
CC(OC([N:8](C(OC(C)(C)C)=O)[N:9]([C:17]1[C:22]([F:23])=[C:21]([N:24]2[CH2:33][CH2:32][N:31]3[C@@H:26]([CH2:27][O:28][CH2:29][CH2:30]3)[CH2:25]2)[N:20]=[C:19]([Cl:34])[N:18]=1)C(OC(C)(C)C)=O)=O)(C)C.Cl.O1CCOCC1>CO>[Cl:34][C:19]1[N:20]=[C:21]([N:24]2[CH2:33][CH2:32][N:31]3[C@@H:26]([CH2:27][O:28][CH2:29][CH2:30]3)[CH2:25]2)[C:22]([F:23])=[C:17]([NH:9][NH2:8])[N:18]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of tris(1,1-dimethylethyl)2-{2-chloro-5-fluoro-6-[(9aR)-hexahydropyrazino[2,1-c][1,4]oxazin-8(1H)-yl]-4-pyrimidinyl}-1,1,2-hydrazinetricarboxylate (4.34 g, 7.20 mmol) in MeOH (18 mL) was added 4 N HCl in dioxane (18 mL, 72 mmol). The solution was stirred for 3 days, and then concentrated in vacuo. The residue was dissolved in water (50 mL) and the solution was adjusted to pH 10 with 20% aq. K2CO3. The mixture was extracted with DCM (2×100 mL), and the combined organic phase was dried over anhydrous Na2SO4, filtered, and concentrated in vacuo to give (9aR)-8-(2-chloro-5-fluoro-6-hydrazino-4-pyrimidinyl)octahydropyrazino[2,1-c][1,4]oxazine (1.41 g, 65%) as an orange solid. LCMS: (M+H)+: 303.1.
Workup
- concentrationconcentrated in vacuo
- dissolutionThe residue was dissolved in water (50 mL)
- extractionThe mixture was extracted with DCM (2×100 mL)
- dry with materialthe combined organic phase was dried over anhydrous Na2SO4
- filtrationfiltered
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-df5619bb6cdd479a94de5d4daae2aa8e
- Source dataset
- uspto-grants-2011_02
- Patent number
- US07893056B2
Reaction notes
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