Triethylamine → HCID 86714772, compound

HRID 2171913Notes

Reaction equation

HRID 2171913 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-b658397ed4ae4c1c9a92d8ea7cc2865c
Source dataset
uspto-grants-2015_06
Patent number
US09051319B2

Reaction notes

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