2,5-Dimethoxytetrahydrofuran → HCID 89444977, compound

HRID 526039

Reaction equation

HRID 526039 reaction equation
[F:1][C:2]1[C:7]([NH2:8])=[C:6]([CH3:9])[CH:5]=[CH:4][N:3]=1.CO[CH:12]1[CH2:16][CH2:15][CH:14](OC)O1>C(O)(=O)C>[F:1][C:2]1[C:7]([N:8]2[CH:12]=[CH:16][CH:15]=[CH:14]2)=[C:6]([CH3:9])[CH:5]=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 790982,5-DimethoxytetrahydrofuranHCID 27631612-Fluoro-4-methylpyridin-3-amine

Product 1

HCID 89444977HCID 89444977, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

2-Fluoro-4-methylpyridin-3-amine (1.0 g, 7.93 mmol) and 2,5-dimethoxytetrahydrofuran (1.08 mL, 1.05 equiv.) were suspended in 3 mL of acetic acid and refluxed for 2 hours. The reaction was cooled down to room temperature. The solvents were removed and the residue was purified by silica gel chromatography (EtOAc/hexanes=1:8, Rf=0.3) to afford 1.0 g (72%) oil. 1H NMR (400 MHz, CDCl3) δ 8.10 (dd, J=0.8, 5.1 Hz, 1H), 7.17 (d, J=5.1 Hz, 1H), 6.74 (td, J=2.1, 0.9 Hz, 2H), 6.40 (t, J=2.1 Hz, 2H), 2.26 (s, 3H). 13C NMR (101 MHz, CDCl3) δ 160.2, 157.8, 149.6, 149.5, 145.5, 145.4, 123.80, 123.76, 122.1, 109.8, 17.29, 17.25. HRMS (m/z) calcd for C10H10FN2 (M+H) 177.0828. found 177.0827. Richards, et al. (2008) Bioorg. & Med. Chem. Lett. 18:4325-27.

Workup

  1. temperaturerefluxed for 2 hours
  2. customThe solvents were removed
  3. customthe residue was purified by silica gel chromatography (EtOAc/hexanes=1:8, Rf=0.3)

Sources & evidence

ORD record
ord-d35e028e63194464a24ed6cd4aa09f52
Source dataset
uspto-grants-2016_05
Patent number
US09345703B2

Linked notes

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