Hydrochloric Acid → (3S)-4-(5-fluoro-6-hydrazino-2-methyl-4-pyrimidinyl)-3-methylmorpholine dihydrochloride

HRID 1366683Notes

Reaction equation

HRID 1366683 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[CH2:29][CH2:28][O:27][CH2:26][C@@H:25]2[CH3:30])[N:20]=[C:19]([Cl:31])[N:18]=1)C(OC(C)(C)C)=O)=O)(C)C.[ClH:39].[CH3:40]COCC>C(Cl)Cl>[ClH:31].[ClH:39].[F:23][C:22]1[C:21]([N:24]2[CH2:29][CH2:28][O:27][CH2:26][C@@H:25]2[CH3:30])=[N:20][C:19]([CH3:40])=[N:18][C:17]=1[NH:9][NH2:8]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 86637029tris(1,1-dimethylethyl) 2-{2-chloro-5-fluoro-6-[(3S)-3-methyl-4-morpholinyl]-4-pyrimidinyl}-1,1,2-hydrazinetricarboxylate

Product 1

HCID 66936365(3S)-4-(5-fluoro-6-hydrazino-2-methyl-4-pyrimidinyl)-3-methylmorpholine dihydrochlorideYield 65%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tris(1,1-dimethylethyl)2-{2-chloro-5-fluoro-6-[(3S)-3-methyl-4-morpholinyl]-4-pyrimidinyl}-1,1,2-hydrazinetricarboxylate (0.6552 g, 1.166 mmol) in DCM (12 mL) was added 2 N HCl in Et2O (12 mL, 24 mmol). The solution was stirred for 2 days, and the resulting mixture was concentrated in vacuo. The solid was triturated with Et2O and collected by vacuum filtration to afford (3S)-4-(5-fluoro-6-hydrazino-2-methyl-4-pyrimidinyl)-3-methylmorpholine dihydrochloride (0.2543 g, 65%) as a yellow solid. LCMS: (M+H)+: 262.0.

Workup

  1. concentrationthe resulting mixture was concentrated in vacuo
  2. customThe solid was triturated with Et2O
  3. filtrationcollected by vacuum filtration

Sources & evidence

ORD record
ord-c73d058ec6334c8d8eebbe685a1f4df9
Source dataset
uspto-grants-2011_02
Patent number
US07893056B2

Reaction notes

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