Methylhydrazine → (2-Hydrazino-6-trifluoromethylpyrimidin-4-yl)-methyl-(4-trifluoromethoxy-phenyl)amine

HRID 1907837Notes

Reaction equation

HRID 1907837 reaction equation
Cl[C:2]1[N:7]=[C:6]([N:8]([CH3:20])[C:9]2[CH:14]=[CH:13][C:12]([O:15][C:16]([F:19])([F:18])[F:17])=[CH:11][CH:10]=2)[CH:5]=[C:4]([C:21]([F:24])([F:23])[F:22])[N:3]=1.C[NH:26][NH2:27]>C1COCC1>[NH:26]([C:2]1[N:7]=[C:6]([N:8]([CH3:20])[C:9]2[CH:14]=[CH:13][C:12]([O:15][C:16]([F:19])([F:18])[F:17])=[CH:11][CH:10]=2)[CH:5]=[C:4]([C:21]([F:24])([F:23])[F:22])[N:3]=1)[NH2:27]

Participants

4

Reactant 2

HCID 6061MethylhydrazineHCID 57507179(2-Chloro-6-trifluoromethylpyrimidin-4-yl)-methyl-(4-trifluoromethoxyphenyl)-amine

Product 1

HCID 57507180(2-Hydrazino-6-trifluoromethylpyrimidin-4-yl)-methyl-(4-trifluoromethoxy-phenyl)amineYield 91.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of XXVIII (475 mg, 1.28 mmol) in dry THF (3 mL) was added methylhydrazine (273 μL, 5.13 mmol). The resulting solution was stirred at room temperature for 18 hrs, the solvent removed in vacuo and the residue taken up in CH2Cl2. The CH2Cl2 solution was washed with H2O, dried over MgSO4, filtered and CH2Cl2 evaporated in vacuo to afford XIX as a yellow oil (0.43 g, 88%): 1H NMR (DMSO-d6) δ 7.48 (app s, 2H), 7.47 (app s, 2H), 5.84 (s, 1H), 4.86 (bs, 2H), 3.42 (s, 3H), 3.19 (s, 3H); ESI/MS 381 (M+H), 366 (M−CH3).

Workup

  1. customthe solvent removed in vacuo
  2. washThe CH2Cl2 solution was washed with H2O
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customCH2Cl2 evaporated in vacuo

Sources & evidence

ORD record
ord-6ee511a94b244a08a8c04fca3102b90a
Source dataset
uspto-grants-2013_12
Patent number
US08598182B2

Reaction notes

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