2,4-Dichloro-5-(trifluoromethyl)pyrimidine → 4-chloro-N-[4-(dipropyl phosphoryl)phenyl]-5-(trifluoromethyl)pyrimidin-2-amine

HRID 511430Notes

Reaction equation

HRID 511430 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.ClC1N=C(Cl)C(C(F)(F)F)=CN=1.[CH2:40]([P:43](C1C=CC(N)=CC=1)([CH2:45][CH2:46][CH3:47])=[O:44])[CH2:41][CH3:42]>>[Cl:1][C:2]1[C:7]([C:8]([F:9])([F:10])[F:11])=[CH:6][N:5]=[C:4]([NH:12][C:13]2[CH:14]=[CH:15][C:16]([P:43]([CH2:45][CH2:46][CH3:47])([CH2:40][CH2:41][CH3:42])=[O:44])=[CH:26][CH:27]=2)[N:3]=1

Participants

4

Reactant 3

HCID 27827742,4-Dichloro-5-(trifluoromethyl)pyrimidineHCID 599945404-(Dipropylphosphoryl)aniline2×HCID 86654003Diethyl (4-{[4-chloro-5-(trifluoromethyl)pyrimidin-2-yl]amino}benzyl)phosphonate

Product 1

HCID 866540404-chloro-N-[4-(dipropyl phosphoryl)phenyl]-5-(trifluoromethyl)pyrimidin-2-amine

Procedure

The title compound was prepared according to the procedure for diethyl (4-{[4-chloro-5-(trifluoromethyl)pyrimidin-2-yl]amino}benzyl)phosphonate using 2,4-Dichloro-5-trifluoromethylpyrimidine (101.6 mg, 0.4681 mmol) and 4-(dipropylphosphoryl)aniline (Compound 198B: 116 mg, 0.515 mmol). This was purified on an ISCO Combiflash unit (0-5% MeOH/DCM) to isolate 75 mg of the desired product as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 0.90 (t, J=7.3 Hz, 6H), 1.30 (br. s., 2H), 1.46 (br. s., 2H), 1.76-2.00 (m, 4H), 7.69 (dd, J=10.1, 8.6 Hz, 2H), 7.84 (dd, J=8.7, 1.9 Hz, 2H), 8.87 (s, 1H), 10.89 (s, 1H). MS (ES+): m/z=406.04 (100) 408.01 (35) [MH+]. HPLC: tR=4.01 min (ZQ3, polar—5 min)

Workup

  1. customThe title compound was prepared
  2. customThis was purified on an ISCO Combiflash unit (0-5% MeOH/DCM)

Sources & evidence

ORD record
ord-e547da8c8f204dfc83a341955f01d0f6
Source dataset
uspto-grants-2015_08
Patent number
US09096624B2

Reaction notes

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