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

HRID 2279771Notes

Reaction equation

HRID 2279771 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]([CH2:17][P:18](=[O:25])([O:22][CH2:23][CH3:24])[O:19][CH2:20][CH3:21])=[CH:15][C:14]=2F)[N:3]=1.[Cl:29]C1N=CC(C(F)(F)F)=C(Cl)N=1.C(OP(CC1C=CC(N)=C(Cl)C=1)(=O)OCC)C>>[Cl:29][C:14]1[CH:15]=[C:16]([CH:26]=[CH:27][C:13]=1[NH:12][C:4]1[N:3]=[C:2]([Cl:1])[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][N:5]=1)[CH2:17][P:18](=[O:25])([O:22][CH2:23][CH3:24])[O:19][CH2:20][CH3:21]

Participants

4

Reactant 3

HCID 27827742,4-Dichloro-5-(trifluoromethyl)pyrimidineHCID 19077629Diethyl 3-chloro-4-aminobenzylphosphonate2×HCID 86697719Diethyl (4-{[4-chloro-5-(trifluoromethyl)pyrimidin-2-yl]amino}-3-fluorobenzyl)phosphonate

Product 1

HCID 86697725Diethyl (3-chloro-4-{[4-chloro-5-(trifluoromethyl)pyrimidin-2-yl]amino}benzyl)phosphonateYield 30%

Procedure

Prepared analogously to Compound 22C using 2,6-Dichloro-5-trifluoromethylpyrimidine (2.2 g, 10.3 mmol) and (4-amino-3-chlorobenzyl)phosphonic acid diethyl ester (Compound 24D, 2.2 g, 7.94 mmol) to afford 1.1 g of the title compound (30%). 1H NMR (400 MHz, CDCl3): δ=1.22-1.26 (m, 6H), 3.1 (d, J=22 Hz, 2H), 3.99-4.08 (m, 4H), 7.23 (d, J=8.4 Hz, 1H), 7.36 (s, 1H), 7.83 (brs, 1H), 8.3 (d, J=8.2 Hz, 1H), 8.57 (s, 1H).

Sources & evidence

ORD record
ord-7086ef5d5f674462b0576a9c750cd971
Source dataset
uspto-grants-2015_09
Patent number
US09133224B2

Reaction notes

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