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

HRID 511527Notes

Reaction equation

HRID 511527 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[C:7]([CH2:9][P:10](=[O:17])([O:14][CH2:15][CH3:16])[O:11][CH2:12][CH3:13])[CH:6]=[CH:5][C:4]=1[N+:18]([O-])=O.[H][H]>CO.[Pd]>[NH2:18][C:4]1[CH:5]=[CH:6][C:7]([CH2:9][P:10](=[O:17])([O:14][CH2:15][CH3:16])[O:11][CH2:12][CH3:13])=[N:8][C:3]=1[O:2][CH3:1]

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, 1 H), 6.66 (dd, J=7.7, 2.8 Hz, 1 H), 4.81 (s, 2 H), 3.97 (quin, J=7.3 Hz, 4 H), 3.84 (s, 3 H), 3.13 (d, J=21.2 Hz, 2 H), 1.18 (t, J=7.1 Hz, 6 H). 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-f850f5f6bf6d4eebade193fe60498066
Source dataset
uspto-grants-2015_08
Patent number
US09096624B2

Reaction notes

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