2-Methoxyaniline → HCID 21923109, compound

HRID 511250Notes

Reaction equation

HRID 511250 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][C:14]=2[O:28][CH3:29])[N:3]=1.ClC1N=C(Cl)C(C(F)(F)F)=CN=1.COC1C=CC=CC=1N>>[Cl:1][C:2]1[C:7]([C:8]([F:11])([F:9])[F:10])=[CH:6][N:5]=[C:4]([NH:12][C:13]2[CH:27]=[CH:26][CH:16]=[CH:15][C:14]=2[O:28][CH3:29])[N:3]=1

Participants

4

Reactant 3

HCID 70002-MethoxyanilineHCID 27827742,4-Dichloro-5-(trifluoromethyl)pyrimidineHCID 86654002Diethyl (4-{[4-chloro-5-(trifluoromethyl) pyrimidin-2-yl]amino}-3-methoxybenzyl)phosphonate

Product 1

HCID 21923109HCID 21923109, compoundYield 46%

Procedure

This material was prepared in a manner analogous to diethyl (4-{[4-chloro-5-(trifluoromethyl)pyrimidin-2-yl]amino}-3-methoxybenzyl)phosphonate using commercially available starting materials (2,4-dichloro-5-(trifluoromethyl)pyrimidine and 2-Methoxyaniline). The crude product from this reaction was recrystallized using MeCN to afford a white solid, 610 mg, 46% yield. 1H NMR (CDCl3): 3.93 (s, 3H), 6.94 (dd, J=8.1 Hz, 1.5 Hz, 1H), 7.03 (td, J=7.8 Hz, 1.5 Hz, 1H), 7.10 (td, J=7.6 Hz, 1.8 Hz, 1H), 8.14 (br s, 1H), 8.41 (dd, J=8.1 Hz, 1.8 Hz, 1H), 8.56 (s, 1H). MS (ES+): m/z=304.00 [MH+]. HPLC: tR=3.89 min (ZQ3, polar—5 min).

Workup

  1. customThe crude product from this reaction was recrystallized
  2. customto afford a white solid, 610 mg, 46% yield
  3. custom5 min

Sources & evidence

ORD record
ord-88dd8ea3f9f841f6adaddb573869c133
Source dataset
uspto-grants-2015_08
Patent number
US09096624B2

Reaction notes

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