Hydrochloric Acid → HCID 86637006, compound

HRID 1366618Notes

Reaction equation

HRID 1366618 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[CH2:28][CH:27]([N:29]([CH3:31])[CH3:30])[CH2:26][C:25]2([CH3:33])[CH3:32])[N:20]=[C:19]([Cl:34])[N:18]=1)C(OC(C)(C)C)=O)=O)(C)C.Cl>CO.O1CCOCC1>[Cl:34][C:19]1[N:20]=[C:21]([N:24]2[C:25]([CH3:33])([CH3:32])[CH2:26][CH:27]([N:29]([CH3:30])[CH3:31])[CH2:28]2)[C:22]([F:23])=[C:17]([NH:9][NH2:8])[N:18]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 86637007HCID 86637007, compound

Product 1

HCID 86637006HCID 86637006, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of tris(1,1-dimethylethyl)2-{2-chloro-6-[4-(dimethylamino)-2,2-dimethyl-1-pyrrolidinyl]-5-fluoro-4-pyrimidinyl}-1,1,2-hydrazinetricarboxylate (2.2004 g, 3.648 mmol) in MeOH (22 mL) was added 4 N HCl in dioxane (22 mL). The solution was stirred for 3 days and then concentrated in vacuo. The residue was azeotroped with MeOH (50 mL), and then partitioned between DCM (100 mL) and sat. aq. NaHCO3 (100 mL). The aqueous phase was extracted with fresh DCM (2×50 mL), and the combined organic phase was dried over anhydrous Na2SO4, filtered, and concentrated in vacuo to give 1-(2-chloro-5-fluoro-6-hydrazino-4-pyrimidinyl)-N,N,5,5-tetramethyl-3-pyrrolidinamine (1.0552 g, 96%) as an orange foam. LCMS: (M+H)+: 303.1.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was azeotroped with MeOH (50 mL)
  3. custompartitioned between DCM (100 mL) and sat. aq. NaHCO3 (100 mL)
  4. extractionThe aqueous phase was extracted with fresh DCM (2×50 mL)
  5. dry with materialthe combined organic phase was dried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5bec3d9af8854dd18bf9562eeab6ce8e
Source dataset
uspto-grants-2011_02
Patent number
US07893056B2

Reaction notes

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