Methanol → 8-(3-Acetyl-5-ethoxy-2-methyl-1,4-dihydro-1,6-naphthyridin-4-yl)-2-methyl-4H-chromen-4-one

HRID 1951404Notes

Reaction equation

HRID 1951404 reaction equation
[C:1]([C:4]1[CH:13]([C:14]2[CH:15]=[CH:16][CH:17]=[C:18]3[C:23]=2[O:22][C:21]([CH3:24])=[CH:20][C:19]3=[O:25])[C:12]2[C:11](=[O:26])[NH:10][CH:9]=[CH:8][C:7]=2[NH:6][C:5]=1[CH3:27])(=[O:3])[CH3:2].FC(F)(F)S(O[CH2:34][CH3:35])(=O)=O.CO>C1COCC1>[C:1]([C:4]1[CH:13]([C:14]2[CH:15]=[CH:16][CH:17]=[C:18]3[C:23]=2[O:22][C:21]([CH3:24])=[CH:20][C:19]3=[O:25])[C:12]2[C:7](=[CH:8][CH:9]=[N:10][C:11]=2[O:26][CH2:34][CH3:35])[NH:6][C:5]=1[CH3:27])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 887MethanolHCID 67924Ethyl trifluoromethanesulphonateHCID 596030093-Acetyl-2-methyl-4-(2-methyl-4-oxo-4H-chromen-8-yl)-4,6-dihydro-1,6-naphthyridin-5(1H)-one

Product 1

HCID 247983288-(3-Acetyl-5-ethoxy-2-methyl-1,4-dihydro-1,6-naphthyridin-4-yl)-2-methyl-4H-chromen-4-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

60 mg (0.16 mmol) of 3-acetyl-2-methyl-4-(2-methyl-4-oxo-4H-chromen-8-yl)-4,6-dihydro-1,6-naphthyridin-5(1H)-one are suspended in THF (4 ml), and 0.18 ml (0.18 mmol) of N′″-(tert-butyl)-N,N′,N″-tris[tris(dimethylamino)phosphoranylidene]phosphorimide triamide (phosphazene base P4-t-Bu; 1 M in hexane) is added. Then 25 μl (0.199 mmol) of ethyl trifluoromethanesulfonate are added to the dark red solution. The decolorized solution is stirred for 10 min and then mixed with methanol and concentrated. The residue is purified by preparative HPLC to result in 35 mg (54% of theory) of the title compound as a white solid.

Workup

  1. concentrationconcentrated
  2. customThe residue is purified by preparative HPLC

Sources & evidence

ORD record
ord-b4f1c225a0f347659a8b18c2519dfaff
Source dataset
uspto-grants-2013_03
Patent number
US08404709B2

Reaction notes

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