Hydrazine hydrate (1:1) → HCID 178429473, compound

HRID 576925Notes

Reaction equation

HRID 576925 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-])=O)=[CH:4][C:3]=1[CH2:11][S:12][C:13]1[N:18]=[C:17]([OH:19])[CH:16]=[C:15]([CH3:20])[N:14]=1.O.NN>CCO.[Ni]>[ClH:1].[NH2:8][C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[C:3]([CH2:11][S:12][C:13]2[N:18]=[C:17]([OH:19])[CH:16]=[C:15]([CH3:20])[N:14]=2)[CH:4]=1

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 1784294812-[(2-chloro-5-nitrophenyl)methylsulfanyl]-6-methyl-1H-pyrimidin-4-one

Product 1

HCID 178429473HCID 178429473, compoundYield 17.7%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

To a mixture of 2-{[(2-chloro-5-nitrophenyl)methyl]sulfanyl}-6-methylpyrimidin-4-ol (500 mg, 1.6 mmol) in absolute EtOH (15 mL) was added hydrazine hydrate (1 mL, 32 mmol) and Raney nickel. The reaction mixture was stirred at room temperature overnight. The solid material was filtered on Celite. The pad was recovered and suspended in a mixture of MeOH/EtOAc/CH2Cl2 (100 mL). The mixture was filtered. The filtrate was recovered, evaporated, and dried in vacuo, affording the 2-{[(5-amino-2-chlorophenyl)methyl]sulfanyl}-6-methylpyrimidin-4-ol (45 mg, 10% yield). The product was used without further purification.

Workup

  1. filtrationThe solid material was filtered on Celite
  2. customThe pad was recovered
  3. additionsuspended in a mixture of MeOH/EtOAc/CH2Cl2 (100 mL)
  4. filtrationThe mixture was filtered
  5. customThe filtrate was recovered
  6. customevaporated
  7. customdried in vacuo

Sources & evidence

ORD record
ord-3e3d3be171a34f78b8dfa62a132a465e
Source dataset
uspto-grants-2015_05
Patent number
US09040538B2

Reaction notes

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