Hydrazine hydrate (1:1) → HCID 86686750, compound

HRID 1403118Notes

Reaction equation

HRID 1403118 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N+:8]([O-])=O)[C:3]=1[NH:11][C:12]1[CH:17]=[C:16]([N:18]2[CH2:23][CH2:22][O:21][CH2:20][CH2:19]2)[N:15]=[C:14]([S:24][CH3:25])[N:13]=1.O.NN>C(O)C.[Fe](Cl)Cl>[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([NH2:8])[C:3]=1[NH:11][C:12]1[CH:17]=[C:16]([N:18]2[CH2:23][CH2:22][O:21][CH2:20][CH2:19]2)[N:15]=[C:14]([S:24][CH3:25])[N:13]=1

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 86686749HCID 86686749, compound

Product 1

HCID 86686750HCID 86686750, compoundYield 79.1%

Reagents, catalysts & solvents 2

HCID 24458Ferrous ChlorideCatalystHCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

N-(2-Methyl-6-nitrophenyl)-2-(methylsulfanyl)-6-(morpholin-4-yl)pyrimidin-4-amine (750 mg) was dissolved in ethanol (22.5 mL), and iron chloride (III) hexahydrate (56 mg) and activated carbon (75 mg) were added thereto, followed by stirring at 80° C. Hydrazine monohydrate (0.3 mL) was added dropwise thereto, followed by heating and refluxing overnight. The reaction mixture was cooled to room temperature and filtered through celite. The mother liquid was concentrated and the residue was purified using silica gel column chromatography (hexane:ethyl acetate) to obtain 3-methyl-N2-[2-(methylsulfanyl)-6-(morpholin-4-yl)pyrimidin-4-yl]benzene-1,2-diamine (544 mg) as a pale yellow powder.

Workup

  1. temperatureby heating
  2. temperaturerefluxing overnight
  3. temperatureThe reaction mixture was cooled to room temperature
  4. filtrationfiltered through celite
  5. concentrationThe mother liquid was concentrated
  6. customthe residue was purified

Sources & evidence

ORD record
ord-2de30863fde048a49bad5405520f7f4f
Source dataset
uspto-grants-2014_12
Patent number
US08912180B2

Reaction notes

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