Tris(1,1-dimethylethyl) 2-{2-chloro-5-fluoro-6-[(1-methylethyl)amino]-4-pyrimidinyl}-1,1,2-hydrazinetricarboxylate → 2-chloro-5-fluoro-6-hydrazino-N-(1-methylethyl)-4-pyrimidinamine

HRID 1366397Notes

Reaction equation

HRID 1366397 reaction equation
CC(OC([N:8](C(OC(C)(C)C)=O)[N:9]([C:17]1[C:22]([F:23])=[C:21]([NH:24][CH:25]([CH3:27])[CH3:26])[N:20]=[C:19]([Cl:28])[N:18]=1)C(OC(C)(C)C)=O)=O)(C)C>CO.Cl.O1CCOCC1>[Cl:28][C:19]1[N:20]=[C:21]([NH:24][CH:25]([CH3:27])[CH3:26])[C:22]([F:23])=[C:17]([NH:9][NH2:8])[N:18]=1

Participants

5

Reactant 1

HCID 86636921Tris(1,1-dimethylethyl) 2-{2-chloro-5-fluoro-6-[(1-methylethyl)amino]-4-pyrimidinyl}-1,1,2-hydrazinetricarboxylate

Product 1

HCID 866369222-chloro-5-fluoro-6-hydrazino-N-(1-methylethyl)-4-pyrimidinamine

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of tris(1,1-dimethylethyl)2-{2-chloro-5-fluoro-6-[(1-methylethyl)amino]-4-pyrimidinyl}-1,1,2-hydrazinetricarboxylate (597 mg, 1.15 mmol) in MeOH (5 mL) and 4.0M HCl in dioxane (5 mL) was stirred at room temperature overnight. After filtering away the precipitate, the solvent was removed in vacuo, providing the crude 2-chloro-5-fluoro-6-hydrazino-N-(1-methylethyl)-4-pyrimidinamine, presumably as the tri-HCl salt. LCMS: (M+H)+: 219.9.

Workup

  1. filtrationAfter filtering away the precipitate
  2. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-155e618fd82d4596bd99110e4871bfdf
Source dataset
uspto-grants-2011_02
Patent number
US07893056B2

Reaction notes

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