Hydrazine hydrate (1:1) → HCID 66936055, compound

HRID 1366476Notes

Reaction equation

HRID 1366476 reaction equation
Cl[C:2]1[C:7]([F:8])=[C:6]([N:9]2[CH2:14][CH2:13][N:12]([CH3:15])[CH2:11][C@H:10]2[CH3:16])[N:5]=[C:4]([CH3:17])[N:3]=1.O.[NH2:19][NH2:20]>O1CCOCC1>[CH3:16][C@@H:10]1[CH2:11][N:12]([CH3:15])[CH2:13][CH2:14][N:9]1[C:6]1[C:7]([F:8])=[C:2]([NH:19][NH2:20])[N:3]=[C:4]([CH3:17])[N:5]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 86636952HCID 86636952, compound

Product 1

HCID 66936055HCID 66936055, compoundYield 100.7%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
85 °C

Procedure

To a solution of 4-chloro-6-[(2R)-2,4-dimethyl-1-piperazinyl]-5-fluoro-2-methylpyrimidine (9.6 g, assumed 31.4 mmol) in 1,4-dioxane (126 mL) was added hydrazine monohydrate (8.5 mL, 175 mmol). The mixture was heated at 85° C. and stirred for 24 h. The mixture was cooled to room temperature and then concentrated in vacuo. The residue was partitioned between DCM (200 mL) and sat. aq. NaHCO3 (100 mL). The aqueous phase was extracted with a fresh portion of DCM (50 mL), and the combined organic phase was dried over anhydrous Na2SO4, filtered, and concentrated in vacuo to give crude 4-[(2R)-2,4-dimethyl-1-piperazinyl]-5-fluoro-6-hydrazino-2-methylpyrimidine (8.04 g, >100% crude yield) as a dark orange oil. LCMS: (M+H)+: 254.9.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. concentrationconcentrated in vacuo
  3. customThe residue was partitioned between DCM (200 mL) and sat. aq. NaHCO3 (100 mL)
  4. extractionThe aqueous phase was extracted with a fresh portion of DCM (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-afa364e0a8334a568692cc40c8a038e4
Source dataset
uspto-grants-2011_02
Patent number
US07893056B2

Reaction notes

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