Diethyl[(6-methoxy-5-nitropyridin-2-yl)methyl]phosphonate → Diethyl[(5-amino-6-methoxypyridin-2-yl)methyl]phosphonate

HRID 1948096Notes

Reaction equation

HRID 1948096 reaction equation
[CH2:1]([O:3][P:4]([CH2:9][C:10]1[CH:15]=[CH:14][C:13]([N+:16]([O-])=O)=[C:12]([O:19][CH3:20])[N:11]=1)(=[O:8])[O:5][CH2:6][CH3:7])[CH3:2].[H][H]>CO.[Pd]>[CH2:1]([O:3][P:4]([CH2:9][C:10]1[CH:15]=[CH:14][C:13]([NH2:16])=[C:12]([O:19][CH3:20])[N:11]=1)(=[O:8])[O:5][CH2:6][CH3:7])[CH3:2]

Participants

5

Reactant 2

HCID 86654057Diethyl[(6-methoxy-5-nitropyridin-2-yl)methyl]phosphonate2×HCID 178418361HCID 178418361, compound

Product 1

HCID 86654056Diethyl[(5-amino-6-methoxypyridin-2-yl)methyl]phosphonateYield 93.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of diethyl[(6-methoxy-5-nitropyridin-2-yl)methyl]phosphonate (Compound 286C, 750 mg, 2.465 mmol) and Pd/C (0.247 mmol) in 3 mL methanol was stirred under 1 atmosphere of hydrogen at room temperature overnight. The crude mixture was filtered through celite and the product (630 mg, 93% yield) was used directly in next step. 1H NMR (DMSO-d6) δ=6.82 (d, J=7.6 Hz, 1H), 6.66 (dd, J=7.7, 2.8 Hz, 1H), 4.81 (s, 2H), 3.97 (quin, J=7.3 Hz, 4H), 3.84 (s, 3H), 3.13 (d, J=21.2 Hz, 2H), 1.18 (t, J=7.1 Hz, 6H). MS (ES+): m/z 275.19 (100) [MH+]; HPLC: tR=0.81 min (UPLC, Analytical).

Workup

  1. filtrationThe crude mixture was filtered through celite

Sources & evidence

ORD record
ord-391a4cd4e7cc464485668b95ba5d297a
Source dataset
uspto-grants-2013_03
Patent number
US08399433B2

Reaction notes

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