Hydrazine hydrate (1:1) → 4-(6-Hydrazinylpyrimidin-4-yl)-1,4-oxazepane

HRID 2039482Notes

Reaction equation

HRID 2039482 reaction equation
O.[NH2:2][NH2:3].Cl[C:5]1[N:10]=[CH:9][N:8]=[C:7]([N:11]2[CH2:17][CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)[CH:6]=1>C(O)C>[NH:2]([C:5]1[N:10]=[CH:9][N:8]=[C:7]([N:11]2[CH2:17][CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)[CH:6]=1)[NH2:3]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 579250744-(6-Chloropyrimidin-4-yl)-1,4-oxazepane

Product 1

HCID 579250704-(6-Hydrazinylpyrimidin-4-yl)-1,4-oxazepane

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

At RT, 8.8 ml (9.0 g, 180.2 mmol) of hydrazine hydrate are added dropwise with stirring to a solution of 3.9 g (18.0 mmol) of 4-(6-chloropyrimidin-4-yl)-1,4-oxazepane in 25 ml of ethanol. After 16 h of stirring at 80° C., the reaction solution is concentrated under reduced pressure. The residue is triturated with cold ethanol, the precipitated solid is filtered off and the filter residue is washed with 25 ml of diethyl ether. The product is dried under reduced pressure. Yield: 1.4 g (36% of theory)

Workup

  1. concentrationthe reaction solution is concentrated under reduced pressure
  2. customThe residue is triturated with cold ethanol
  3. filtrationthe precipitated solid is filtered off
  4. washthe filter residue is washed with 25 ml of diethyl ether
  5. customThe product is dried under reduced pressure

Sources & evidence

ORD record
ord-cd739734ec2248e0a66815e192b1dd84
Source dataset
uspto-grants-2013_11
Patent number
US08580778B2

Reaction notes

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