Hydrazine hydrate (1:1) → HCID 178429436, compound

HRID 576946Notes

Reaction equation

HRID 576946 reaction equation
[Cl:1][C:2]1[C:7]([N+:8]([O-])=O)=[CH:6][CH:5]=[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.C(Cl)Cl.O.[Ni]>[NH2:8][C:7]1[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]=[CH:5][CH:6]=1

Participants

6

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 1784294392-[(2-chloro-3-nitrophenyl)methylsulfanyl]-6-methyl-1H-pyrimidin-4-one

Product 1

HCID 178429436HCID 178429436, compoundYield 7%

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 962WaterSolventHCID 21584144Dichloromethane ethanolSolvent

Procedure

2-{[(2-chloro-3-nitrophenyl)methyl]sulfanyl}-6-methylpyrimidin-4-ol (150 mg, 481 mmol) was dissolved in 1:1 EtOH/DCM (6 mL). Hydrazine hydrate (224 mL, 7.2 mmol) and catalytic amount of Ni-Raney solution in water were added. The mixture was stirred overnight at room temperature. The solid material was filtered on Celite and washed with methanol and ethyl acetate. The filtrate was evaporated. The residue was dissolved in DCM and purified on silica gel using 10% DCM/MeOH to afford 2-{[(3-amino-2-chlorophenyl)methyl]sulfanyl}-6-methylpyrimidin-4-ol (10 mg, 7% yield); 1H NMR (400 MHz, DMSO-d6): δ 2.21 (s, 3H), 4.39 (s, 2H), 5.41 (s, 2H), 5.98 (bs, 1H), 6.70-6.75 (m, 2H), 6.95 (t, J=7.7 Hz, 1H); LRMS (ES+) m/z 282 (100%, M+1), 284 (35%, M+3).

Workup

  1. filtrationThe solid material was filtered on Celite
  2. washwashed with methanol and ethyl acetate
  3. customThe filtrate was evaporated
  4. dissolutionThe residue was dissolved in DCM
  5. custompurified on silica gel using 10% DCM/MeOH

Sources & evidence

ORD record
ord-22052fd9c8ab47508bfe4684516944e2
Source dataset
uspto-grants-2015_05
Patent number
US09040538B2

Reaction notes

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