Diethyl p-aminobenzylphosphonate → Diethyl (4-{[4-chloro-5-(trifluoromethyl)pyrimidin-2-yl]amino}benzyl)phosphonate

HRID 511248Notes

Reaction equation

HRID 511248 reaction equation
[Cl:1][C:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][N:5]=[C:4]([NH:12][C:13]2[CH:27]=[CH:26][C:16]([CH2:17][P:18](=[O:25])([O:22][CH2:23][CH3:24])[O:19][CH2:20][CH3:21])=[CH:15][C:14]=2OC)[N:3]=1.C(OP(CC1C=CC(N)=CC=1)(=O)OCC)C>>[Cl:1][C:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][N:5]=[C:4]([NH:12][C:13]2[CH:27]=[CH:26][C:16]([CH2:17][P:18](=[O:25])([O:22][CH2:23][CH3:24])[O:19][CH2:20][CH3:21])=[CH:15][CH:14]=2)[N:3]=1

Participants

3

Reactant 2

HCID 88358Diethyl p-aminobenzylphosphonateHCID 86654002Diethyl (4-{[4-chloro-5-(trifluoromethyl) pyrimidin-2-yl]amino}-3-methoxybenzyl)phosphonate

Product 1

HCID 86654003Diethyl (4-{[4-chloro-5-(trifluoromethyl)pyrimidin-2-yl]amino}benzyl)phosphonate

Procedure

Prepared in a manner analogous to that for diethyl (4-{[4-chloro-5-(trifluoromethyl)pyrimidin-2-yl]amino}-3-methoxybenzyl)phosphonate using commercially available diethyl(4-aminobenzyl)phosphonate in place of diethyl (4-amino-3-methoxybenzyl)phosphonate. Following chromatography, the semi-pure product was crystallized from ethyl acetate to afford the title compound. 1H NMR (400 MHz, METHANOL-d4) d ppm 1.22-1.32 (m, 6 H), 3.17-3.28 (m, 2 H), 3.98-4.10 (m, 4 H), 7.30 (dd, J=8.72, 2.65 Hz, 2 H), 7.65 (d, J=7.83 Hz, 2 H), 8.63 (s, 1 H).

Workup

  1. customthe semi-pure product was crystallized from ethyl acetate

Sources & evidence

ORD record
ord-8381ed520fbd410c9ac4a62fcc0fe671
Source dataset
uspto-grants-2015_08
Patent number
US09096624B2

Reaction notes

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