Triethyl Phosphate → (3-Benzyloxy-6-methoxy-[1,5]naphthyridin-4-ylmethyl)-phosphonic acid diethyl ester

HRID 633801Notes

Reaction equation

HRID 633801 reaction equation
[P:1]([O:9][CH2:10][CH3:11])([O:6][CH2:7][CH3:8])([O:3]CC)=O.[CH2:12]([O:19][C:20]1[C:29]([CH2:30]Br)=[C:28]2[C:23]([CH:24]=[CH:25][C:26]([O:32][CH3:33])=[N:27]2)=[N:22][CH:21]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(OCC)(=O)C>C1(C)C=CC=CC=1>[CH2:10]([O:9][P:1]([CH2:30][C:29]1[C:28]2[C:23](=[CH:24][CH:25]=[C:26]([O:32][CH3:33])[N:27]=2)[N:22]=[CH:21][C:20]=1[O:19][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)(=[O:3])[O:6][CH2:7][CH3:8])[CH3:11]

Participants

5

Reactant 3

HCID 6535Triethyl PhosphateHCID 8857Ethyl AcetateHCID 867306967-Benzyloxy-8-bromomethyl-2-methoxy-[1,5]naphthyridine

Product 1

HCID 86730697(3-Benzyloxy-6-methoxy-[1,5]naphthyridin-4-ylmethyl)-phosphonic acid diethyl esterYield 79%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Triethyl phosphate (960 μL, 5.60 mmol, 10.0 eq) is added at room temperature to a stirred solution of 7-benzyloxy-8-bromomethyl-2-methoxy-[1,5]naphthyridine (200 mg, 0.56 mmol, 1.0 eq) in toluene (1 mL) and the resulting mixture is heated under reflux for 6 hours. Solvent is then removed and the residue is purified by column chromatography (silica gel, eluent: petroleum ether:ethyl acetate, 1:1, v/v) to afford (3-benzyloxy-6-methoxy-[1,5]naphthyridin-4-ylmethyl)-phosphonic acid diethyl ester as a yellow oil (180 mg, 79% yield).

Workup

  1. temperaturethe resulting mixture is heated
  2. temperatureunder reflux for 6 hours
  3. customSolvent is then removed
  4. customthe residue is purified by column chromatography (silica gel, eluent

Sources & evidence

ORD record
ord-651b0c7bf53a43898deba8ebdd5daa70
Source dataset
uspto-grants-2016_04
Patent number
US09321788B2

Reaction notes

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