Hydrochloric Acid → racemic 3-(2-chloro-5-fluoro-6-hydrazino-4-pyrimidinyl)-N,N-dimethyl-3-azabicyclo[3.1.0]hexan-1-amine

HRID 1366548Notes

Reaction equation

HRID 1366548 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][CH:28]3[C:26]([N:30]([CH3:32])[CH3:31])([CH2:27]3)[CH2:25]2)[N:20]=[C:19]([Cl:33])[N:18]=1)C(OC(C)(C)C)=O)=O)(C)C.Cl>CO.O1CCOCC1>[Cl:33][C:19]1[N:20]=[C:21]([N:24]2[CH2:29][CH:28]3[C:26]([N:30]([CH3:32])[CH3:31])([CH2:27]3)[CH2:25]2)[C:22]([F:23])=[C:17]([NH:9][NH2:8])[N:18]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 87210351Racemic tris(1,1-dimethylethyl) 2-{2-chloro-6-[1-(dimethylamino)-3-azabicyclo[3.1.0]hex-3-yl]-5-fluoro-4-pyrimidinyl}-1,1,2-hydrazinetricarboxylate

Product 1

HCID 87210194racemic 3-(2-chloro-5-fluoro-6-hydrazino-4-pyrimidinyl)-N,N-dimethyl-3-azabicyclo[3.1.0]hexan-1-amineYield 53%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of racemic tris(1,1-dimethylethyl)2-{2-chloro-6-[1-(dimethylamino)-3-azabicyclo[3.1.0]hex-3-yl]-5-fluoro-4-pyrimidinyl}-1,1,2-hydrazinetricarboxylate (1.3231 g, 2.254 mmol) in MeOH (13 mL) was added 4 N HCl in dioxane (13 mL). The solution was stirred for 3 days, and was then concentrated in vacuo. The residue was partitioned between 10% aq. K2CO3 and DCM, and the aqueous phase was extracted with a fresh portion of DCM. The combined organic phase was dried over anhydrous Na2SO4, filtered, and concentrated in vacuo to give racemic 3-(2-chloro-5-fluoro-6-hydrazino-4-pyrimidinyl)-N,N-dimethyl-3-azabicyclo[3.1.0]hexan-1-amine (0.3415 g, 53%) as a brown solid. LCMS: (M+H)+: 287.1.

Workup

  1. concentrationwas then concentrated in vacuo
  2. customThe residue was partitioned between 10% aq. K2CO3 and DCM
  3. extractionthe aqueous phase was extracted with a fresh portion of DCM
  4. dry with materialThe combined organic phase was dried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f01195ba8dd34f9ebbf9cf92dc5cd894
Source dataset
uspto-grants-2011_02
Patent number
US07893056B2

Reaction notes

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