3-Furanol, tetrahydro- → HCID 21912086, compound

HRID 1831626Notes

Reaction equation

HRID 1831626 reaction equation
[OH:1][CH:2]1[CH2:6][CH2:5][O:4][CH2:3]1.[H-].[Na+].Cl[C:10]1[N:15]=[C:14]([CH3:16])[N:13]=[C:12]([NH:17][C:18]2[C:23]([CH3:24])=[CH:22][C:21]([CH3:25])=[CH:20][C:19]=2[CH3:26])[C:11]=1[CH3:27]>C1COCC1>[CH3:16][C:14]1[N:13]=[C:12]([NH:17][C:18]2[C:19]([CH3:26])=[CH:20][C:21]([CH3:25])=[CH:22][C:23]=2[CH3:24])[C:11]([CH3:27])=[C:10]([O:1][CH:2]2[CH2:6][CH2:5][O:4][CH2:3]2)[N:15]=1

Participants

5

Reactant 3

HCID 99603-Furanol, tetrahydro-HCID 24758Sodium hydrideHCID 21912049HCID 21912049, compound

Product 1

HCID 21912086HCID 21912086, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 3-hydroxy-tetrahydrofuran (0.5 ml) and sodium hydride (60% in oil, 53 mg, 1.33 mmol) in dry THF was stirred at room temperature for 5 minutes, (6-chloro-2,5-dimethyl-pyrimidin-4-yl)-(2,4,6-trimethylphenyl)-amine (107 mg, 0.388 mmol) was added. The mixture was heated at reflux for 15 hours. The mixture was quenched with water and extracted with ethyl acetate. The organic layer was separated, dried and concentrated to give a yellow oil. The oil was purified through silica gel column chromatography using 20% ethyl acetate in hexane as eluent to give 48 mg of the title compound as off-white crystals, mp 126–128° C. 1H NMR (CDCl3) δ 6.89 (s, 2H), 5.60 (brs, 2H), 3.84.0 (m, 4H), 2.27 (s, 6H), 2.13 (s, 6H), 2.1–2.25 (m, 2H), 1.93 (s, 3H) ppm.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 15 hours
  3. customThe mixture was quenched with water
  4. extractionextracted with ethyl acetate
  5. customThe organic layer was separated
  6. customdried
  7. concentrationconcentrated
  8. customto give a yellow oil
  9. customThe oil was purified through silica gel column chromatography

Sources & evidence

ORD record
ord-31f32a26a25a4f33a9476a90702d05d7
Source dataset
uspto-grants-2006_06
Patent number
US07067664B1

Reaction notes

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