2,4-Dichloro-5-(trifluoromethyl)pyrimidine → Bis(2,2,2-trifluoroethyl) (4-{[4-chloro-5-(trifluoromethyl)pyrimidin-2-yl]amino}benzyl)phosphonate

HRID 511388Notes

Reaction equation

HRID 511388 reaction equation
[Cl:1][C:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][N:5]=[C:4](NC2C=CC(CP(=O)(OCC)OCC)=CC=2)[N:3]=1.[F:28][C:29]([F:49])([F:48])[CH2:30][O:31][P:32]([CH2:40][C:41]1[CH:46]=[CH:45][C:44]([NH2:47])=[CH:43][CH:42]=1)(=[O:39])[O:33][CH2:34][C:35]([F:38])([F:37])[F:36].ClC1N=C(Cl)C(C(F)(F)F)=CN=1>>[Cl:1][C:2]1[C:7]([C:8]([F:10])([F:9])[F:11])=[CH:6][N:5]=[C:4]([NH:47][C:44]2[CH:45]=[CH:46][C:41]([CH2:40][P:32](=[O:39])([O:33][CH2:34][C:35]([F:36])([F:37])[F:38])[O:31][CH2:30][C:29]([F:28])([F:48])[F:49])=[CH:42][CH:43]=2)[N:3]=1

Participants

4

Reactant 3

HCID 27827742,4-Dichloro-5-(trifluoromethyl)pyrimidineHCID 86654003Diethyl (4-{[4-chloro-5-(trifluoromethyl)pyrimidin-2-yl]amino}benzyl)phosphonateHCID 86654030(4-Aminobenzyl)phosphonic acid bis-(2,2,2-trifluoroethyl) ester2×

Product 1

HCID 86654029Bis(2,2,2-trifluoroethyl) (4-{[4-chloro-5-(trifluoromethyl)pyrimidin-2-yl]amino}benzyl)phosphonate

Procedure

The title compound was prepared according to the procedure for diethyl (4-{[4-chloro-5-(trifluoromethyl)pyrimidin-2-yl]amino}benzyl)phosphonate using (4-Aminobenzyl)phosphonic acid bis-(2,2,2-trifluoroethyl) ester (Compound 165B) and 2,4-dichloro-5-(trifluoromethyl)pyrimidine. The desired product was isolated using MDP (ammonium bicarbonate basic buffer pH 9). 1H NMR (400 MHz, DMSOd6) δ ppm 10.69 (s, 1H), 8.81 (s, 1H), 7.65 (d, J=8.1 Hz, 2H), 7.26 (dd, J=8.7, 2.7 Hz, 2H), 4.56-4.72 (m, 4H), 3.51 (d, J=22.2 Hz, 2H). MS (ES+): m/z 532.01/534.02 (100/64) [MH+]. HPLC: tR=1.70 min (TOF, polar—3 min).

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-daecfbfb8f1a4aacac76d85de8841751
Source dataset
uspto-grants-2015_08
Patent number
US09096624B2

Reaction notes

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