2,4-Dichloro-5-(trifluoromethyl)pyrimidine → 4-chloro-N-[3-(dipropylphosphoryl)phenyl]-5-(trifluoromethyl)pyrimidin-2-amine

HRID 511395Notes

Reaction equation

HRID 511395 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.[CH2:28]([P:31](C1C=C(C=CC=1)N)([CH2:33][CH2:34][CH3:35])=[O:32])[CH2:29][CH3:30].ClC1N=C(Cl)C(C(F)(F)F)=CN=1>>[Cl:1][C:2]1[C:7]([C:8]([F:10])([F:11])[F:9])=[CH:6][N:5]=[C:4]([NH:12][C:13]2[CH:14]=[CH:15][CH:16]=[C:26]([P:31]([CH2:33][CH2:34][CH3:35])([CH2:28][CH2:29][CH3:30])=[O:32])[CH:27]=2)[N:3]=1

Participants

4

Reactant 3

HCID 27827742,4-Dichloro-5-(trifluoromethyl)pyrimidineHCID 672552723-(Dipropylphosphoryl)aniline2×HCID 86654003Diethyl (4-{[4-chloro-5-(trifluoromethyl)pyrimidin-2-yl]amino}benzyl)phosphonate

Product 1

HCID 866540324-chloro-N-[3-(dipropylphosphoryl)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 3-(dipropylphosphoryl) aniline (Compound 168C) and 2,4-dichloro-5-trifluoromethylpyrimidine. 1H NMR (400 MHz, CHLOROFORM-d) δ 1.00 (td, J=7.26, 0.88 Hz, 6H), 1.47-1.58 (m, 2H), 1.64-1.77 (m, 2H), 1.82-1.94 (m, 2H), 1.97-2.10 (m, 2H), 7.33-7.40 (m, 1H), 7.51 (td, J=7.83, 3.28 Hz, 1H), 8.00 (d, J=8.34 Hz, 1 H), 8.08 (d, J=12.13 Hz, 1 H), 8.60 (s, 1 H). MS (ES+): m/z=405.97 (100) [MH+]. HPLC: tR=3.47 min (polar—5 min).

Workup

  1. customHPLC: tR=3.47 min (polar—5 min)

Sources & evidence

ORD record
ord-cce7f398b9874defb3e2289bef774e29
Source dataset
uspto-grants-2015_08
Patent number
US09096624B2

Reaction notes

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