2,4-Dichloro-5-(trifluoromethyl)pyrimidine → HCID 178476792, compound

HRID 1947973Notes

Reaction equation

HRID 1947973 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](CP(=O)(OCC)OCC)=[CH:15][CH:14]=2)[N:3]=1.C([P:30]([CH2:33][CH2:34]C1C=CC(N)=CC=1)(=[O:32])[O-:31])C.ClC1N=C(Cl)[C:46](C(F)(F)F)=[CH:45]N=1>>[CH2:45]([O:31][PH:30]([CH2:33][CH2:34][C:16]1[CH:15]=[CH:14][C:13]([NH:12][C:4]2[N:3]=[C:2]([Cl:1])[C:7]([C:8]([F:10])([F:11])[F:9])=[CH:6][N:5]=2)=[CH:27][CH:26]=1)=[O:32])[CH3:46]

Participants

4

Reactant 3

HCID 27827742,4-Dichloro-5-(trifluoromethyl)pyrimidineHCID 86654003Diethyl (4-{[4-chloro-5-(trifluoromethyl)pyrimidin-2-yl]amino}benzyl)phosphonateHCID 86761780Ethyl(4-aminobenzyl)methylphosphinate2×

Product 1

HCID 178476792HCID 178476792, compoundYield 61%

Procedure

The title compound was prepared according to the procedure for diethyl (4-{[4-chloro-5-(trifluoromethyl)pyrimidin-2-yl]amino}benzyl)phosphonate using ethyl(4-aminobenzyl)methylphosphinate (Compound 174B, 1.08 g, 5.07 mmol) and 2,4-dichloro-5-trifluoromethylpyrimidine. (1.0 g, 4.6 mmol). The compound was purified on an Isco Combiflash eluting with 0 to 10% MeOH in EtOAc. The compound was re-crystallized in EtOAc (˜20 mL) to afford 1.1 g, 61% yield, of the title compound. 1H NMR (400 MHz, DMSO-d6) δ 10.64 (s, 1H), 8.79 (d, J=0.51 Hz, 1H), 7.62 (d, J=8.34 Hz, 2H), 7.25 (dd, J=2.27, 8.59 Hz, 2H), 3.86-4.01 (m, 2H), 3.15 (d, J=17.68 Hz, 2H), 1.31 (d, J=13.64 Hz, 3H), 1.19 (t, J=6.95 Hz, 3H); MS (ES+): m/z: 396.0708 [MH+]. HPLC: tR=1.41 min (UPLC TOF MS: polar—3 min).

Workup

  1. customThe compound was purified on an Isco Combiflash
  2. washeluting with 0 to 10% MeOH in EtOAc
  3. customThe compound was re-crystallized in EtOAc (˜20 mL)
  4. customto afford 1.1 g, 61% yield
  5. customHPLC: tR=1.41 min (UPLC TOF MS: polar—3 min)

Sources & evidence

ORD record
ord-1794e6b867c941acacb73bdca98fba4b
Source dataset
uspto-grants-2013_03
Patent number
US08399433B2

Reaction notes

Loading…