2,4-Dichloro-5-(trifluoromethyl)pyrimidine → Bis(2,2,2-trifluoroethyl) (4-{[4-chloro-5-(trifluoromethyl)pyrimidin-2-yl]amino}-3-methoxybenzyl)phosphonate

HRID 511320Notes

Reaction equation

HRID 511320 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=2OC)[N:3]=1.[F:30][C:31]([F:53])([F:52])[CH2:32][O:33][P:34]([CH2:42][C:43]1[CH:48]=[CH:47][C:46]([NH2:49])=[C:45]([O:50][CH3:51])[CH:44]=1)(=[O:41])[O:35][CH2:36][C:37]([F:40])([F:39])[F:38].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:49][C:46]2[CH:47]=[CH:48][C:43]([CH2:42][P:34](=[O:41])([O:35][CH2:36][C:37]([F:38])([F:39])[F:40])[O:33][CH2:32][C:31]([F:30])([F:52])[F:53])=[CH:44][C:45]=2[O:50][CH3:51])[N:3]=1

Participants

4

Reactant 3

HCID 27827742,4-Dichloro-5-(trifluoromethyl)pyrimidineHCID 86654002Diethyl (4-{[4-chloro-5-(trifluoromethyl) pyrimidin-2-yl]amino}-3-methoxybenzyl)phosphonateHCID 86654014Bis(2,2,2-trifluoroethyl)(4-amino-3-methoxybenzyl)phosphonate2×

Product 1

HCID 86654019Bis(2,2,2-trifluoroethyl) (4-{[4-chloro-5-(trifluoromethyl)pyrimidin-2-yl]amino}-3-methoxybenzyl)phosphonate

Procedure

This compound was prepared using the procedure for diethyl (4-{[4-chloro-5-(trifluoromethyl) pyrimidin-2-yl]amino}-3-methoxybenzyl)phosphonate with Bis(2,2,2-trifluoroethyl) (4-amino-3-methoxybenzyl)phosphonate (Compound 114A) and 2,4-dichloro-5-(trifluoromethyl) pyrimidine. Purified using an ISCO Combiflash system eluting w/20-100% EtOAc in heptane and then MDP (ammonium bicarbonate basic buffer pH9). 1H NMR (DMSOd6) δ ppm 9.73 (s, 1H), 8.69 (s, 1H), 7.47 (d, J=8.0 Hz, 1H), 7.03 (s, 1H), 6.90 (d, J=7.9 Hz, 1H), 4.67 (quin, J=8.5 Hz, 4H), 3.76 (s, 3H), 3.56 (d, J=22.1 Hz, 2H). MS (ES+): m/z 562.00/564.02 (100/38) [MH+]. HPLC: tR=3.86 min (ZQ3, polar—5 min).

Workup

  1. customThis compound was prepared
  2. customPurified
  3. washeluting
  4. custom5 min

Sources & evidence

ORD record
ord-128aa566e2434d8cbed6f82d6208bfa8
Source dataset
uspto-grants-2015_08
Patent number
US09096624B2

Reaction notes

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