Tetrahydrofuran → HCID 21218469, compound

HRID 1585456Notes

Reaction equation

HRID 1585456 reaction equation
[N:1]1[CH:6]=[CH:5][N:4]=[CH:3][C:2]=1[C:7]([CH3:12])=[CH:8][C:9]([O-:11])=[O:10].[CH2:13]1COCC1>[Pd]>[N:1]1[CH:6]=[CH:5][N:4]=[CH:3][C:2]=1[CH:7]([CH3:12])[CH2:8][C:9]([O:11][CH3:13])=[O:10]

Participants

4

Reactant 2

HCID 8028TetrahydrofuranHCID 73768239HCID 73768239, compound

Product 1

HCID 21218469HCID 21218469, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A solution of 11e (2.50 g, 14.03 mmol) in 50 mL dry THF was treated with 10% Pd-C (125.0 mg, 5 wt %) at room temperature under a hydrogen atmosphere (balloon) (30 min). The reaction mixture was then filtered through a Celite plug, washed with EtOAc (150 mL), and concentrated in vacuo. SGC chromatotron (SiO2, 4 mm, 20-50% EtOAc/hexanes) afforded 12e (2.48 g, 2.53 g theoretical, 98%). For 12e: 1H NMR (CDCl3, 250 MHz) d 8.42 (d, 1H, J=1.5 Hz, Pyr C3-H), 8.38 (dd, 1H, J=1.5, 2.5 Hz, Pyr C5-H), 8.31 (d, 1H, J=2.5 Hz, Pyr C6-H), 3.51 (s, 3H, OCH3), 3.39 (m, 1H, J=6.5, 7.0, 8.1 Hz, ArCH), 2.80 (dd, 1H, J=8.1, 16.1 Hz, CHH), 2.54 (dd, 1H, J=6.5, 16.1 Hz, CHH), 1.24 (d, 3H, J=7.0 Hz, CH3); 13C NMR (CDCl3, 125 MHz) d 172.3, 159.6, 143.9, 143.8, 142.4, 51.4, 39.7, 35.2, 20.4; IR (neat) nmax 2978, 2935, 1737, 1473, 1406, 1371, 1280, 1180, 1034, 1015, 849, 769 cm-1. See FIG. 18d.

Workup

  1. filtrationThe reaction mixture was then filtered through a Celite plug
  2. washwashed with EtOAc (150 mL)
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7318f5ed84f14b4a9312e4db8676d4c8
Source dataset
uspto-grants-1999_08
Patent number
US05939268

Reaction notes

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