Hydrochloric Acid → HCID 86636934, compound

HRID 1366427Notes

Reaction equation

HRID 1366427 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][N:27]([CH3:30])[CH2:26][C@H:25]2[CH3:31])[N:20]=[C:19]([Cl:32])[N:18]=1)C(OC(C)(C)C)=O)=O)(C)C.Cl.CCOCC>C(Cl)Cl>[Cl:32][C:19]1[N:20]=[C:21]([N:24]2[CH2:29][CH2:28][N:27]([CH3:30])[CH2:26][C@H:25]2[CH3:31])[C:22]([F:23])=[C:17]([NH:9][NH2:8])[N:18]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 86636933HCID 86636933, compound

Product 1

HCID 86636934HCID 86636934, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tris(1,1-dimethylethyl)2-{2-chloro-6-[(2R)-2,4-dimethyl-1-piperazinyl]-5-fluoro-4-pyrimidinyl}-1,1,2-hydrazinetricarboxylate (215.28 g, 374.3 mmol) in DCM (1870 mL) was added 2 N HCl in Et2O (1870 mL, 3740 mmol). The solution was mechanically stirred for 64 h, and the resulting suspension was allowed to settle. Most of the solvent was then decanted, and the remaining solid was triturated with DCM (1000 mL) and collected by vacuum filtration. The solid was washed with DCM and dried under high vacuum to provide 2-chloro-4-[(2R)-2,4-dimethyl-1-piperazinyl]-5-fluoro-6-hydrazinopyrimidine, assumed trihydrochloride (138.22 g, 96% yield) as a light yellow powder. LCMS: (M+H)+: 275.1.

Workup

  1. customMost of the solvent was then decanted
  2. customthe remaining solid was triturated with DCM (1000 mL)
  3. filtrationcollected by vacuum filtration
  4. washThe solid was washed with DCM
  5. customdried under high vacuum

Sources & evidence

ORD record
ord-5cafb09d7c004d488e514acf3063fae3
Source dataset
uspto-grants-2011_02
Patent number
US07893056B2

Reaction notes

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