4-Chloro-3-(trifluoromethyl)aniline → 4-Pyrimidinamine, 2-chloro-N-[4-chloro-3-(trifluoromethyl)phenyl]-5-fluoro-

HRID 733780Notes

Reaction equation

HRID 733780 reaction equation
ClC1N=C(NC2C=CC=C(C3NN=NN=3)C=2)C(F)=CN=1.[Cl:21][C:22]1[N:27]=[C:26](Cl)[C:25]([F:29])=[CH:24][N:23]=1.[Cl:30][C:31]1[CH:37]=[CH:36][C:34]([NH2:35])=[CH:33][C:32]=1[C:38]([F:41])([F:40])[F:39]>>[Cl:21][C:22]1[N:27]=[C:26]([NH:35][C:34]2[CH:36]=[CH:37][C:31]([Cl:30])=[C:32]([C:38]([F:41])([F:39])[F:40])[CH:33]=2)[C:25]([F:29])=[CH:24][N:23]=1

Participants

4

Reactant 3

HCID 675744-Chloro-3-(trifluoromethyl)anilineHCID 2507052,4-Dichloro-5-fluoropyrimidineHCID 178505996HCID 178505996, compound

Product 1

HCID 220609674-Pyrimidinamine, 2-chloro-N-[4-chloro-3-(trifluoromethyl)phenyl]-5-fluoro-

Procedure

In like manner to, the preparation of 2-chloro-5-fluoro-N4-[3-(1H-tetrazol-5-yl)phenyl]-4-pyrimidineamine the reaction of 2,4-dichloro-5-fluoropyrimidine with 4-chloro-3-trifluoromethylaniline gave 2-chloro-N4-(4-chloro-3-trifluoromethylphenyl)-5-fluoro-4-pyrimidineamine. 1H NMR (CDCl3): δ 8.15 (d, 1H, J=2.1 Hz), 7.96 (d, 1H, J=3 Hz), 7.91 (dd, 1H, J=2.7 Hz and 8.7 Hz), 7.53 (d, 1H, J=8.1 Hz), 7.06 (bs, 1H); 19F NMR (CDCl3): −17892 and −44402; LCMS: purity: 93%; MS (m/e): 326 (M+).

Sources & evidence

ORD record
ord-a0875840510a45aa8d681ce5e572fbbb
Source dataset
uspto-grants-2009_09
Patent number
US07589200B2

Reaction notes

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