Triethylamine → HCID 86714772, compound

HRID 1055118Notes

Reaction equation

HRID 1055118 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[C:5]([F:9])=[CH:4][N:3]=1.Cl.[C:11]([NH:15][NH2:16])([CH3:14])([CH3:13])[CH3:12].C(N(CC)CC)C>C1COCC1.CCO>[C:11]([NH:15][NH:16][C:6]1[C:5]([F:9])=[CH:4][N:3]=[C:2]([Cl:1])[N:7]=1)([CH3:14])([CH3:13])[CH3:12]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 81889tert-Butylhydrazine monohydrochlorideHCID 2507052,4-Dichloro-5-fluoropyrimidine

Product 1

HCID 86714772HCID 86714772, compoundYield 77.7%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2,4-dichloro-5-fluoro-pyrimidine (1.84 g, 11.00 mmol) and tert-butylhydrazine hydrochloride (1.25 g, 10.00 mmol) in THF (50 mL) and EtOH (5 mL) was added triethylamine (4.18 mL, 30.00 mmol). The reaction mixture was stirred at room temperature overnight. The reaction mixture was filtered to remove triethylamine HCl salt and the filtrate concentrated in vacuo. The resulting residue was purified by silica gel chromatography (EtOAc/Hexanes) to afford 1.7 g of the desired product: 1H NMR (400 MHz, CDCl3) δ 7.82 (d, J=2.8 Hz, 1H), 6.47 (s, 1H), 4.60 (d, J=5.8 Hz, 1H), 1.09 (s, 9H). LCMS Gradient 10-90%, 0.1% formic acid, 5 minutes, C18/ACN, Retention Time=2.19 minutes (M+H) 218.81.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customto remove triethylamine HCl salt
  3. concentrationthe filtrate concentrated in vacuo
  4. customThe resulting residue was purified by silica gel chromatography (EtOAc/Hexanes)

Sources & evidence

ORD record
ord-63be884be57c460990af5b36b8f7d901
Source dataset
uspto-grants-2016_07
Patent number
US09394302B2

Reaction notes

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