Diethyl p-aminobenzylphosphonate → Diethyl (4-{[4-chloro-5-(trifluoromethyl)pyrimidin-2-yl]amino}benzyl)phosphonate
Reaction equation
[CH2:1]([O:3][P:4]([CH2:9][C:10]1[CH:15]=[CH:14][C:13]([NH:16][C:17]2[N:22]=[C:21]([Cl:23])[C:20]([C:24]([F:27])([F:26])[F:25])=[CH:19][N:18]=2)=[C:12](OC)[CH:11]=1)(=[O:8])[O:5][CH2:6][CH3:7])[CH3:2].C(OP(CC1C=CC(N)=CC=1)(=O)OCC)C>>[CH2:6]([O:5][P:4]([CH2:9][C:10]1[CH:11]=[CH:12][C:13]([NH:16][C:17]2[N:22]=[C:21]([Cl:23])[C:20]([C:24]([F:25])([F:27])[F:26])=[CH:19][N:18]=2)=[CH:14][CH:15]=1)(=[O:8])[O:3][CH2:1][CH3:2])[CH3:7]Participants
3
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, 6H), 3.17-3.28 (m, 2H), 3.98-4.10 (m, 4H), 7.30 (dd, J=8.72, 2.65 Hz, 2H), 7.65 (d, J=7.83 Hz, 2H), 8.63 (s, 1H).
Workup
- customthe semi-pure product was crystallized from ethyl acetate
Sources & evidence
- ORD record
- ord-e6929d6c9dc64f918732efda35ae3340
- Source dataset
- uspto-grants-2013_03
- Patent number
- US08399433B2
Reaction notes
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