2,4-Dichloro-5-fluoropyrimidine → 2-chloro-5-fluoro-N4-(4-methyl-3-trifluoromethylphenyl)-4-pyrimidineamine

HRID 76424Notes

Reaction equation

HRID 76424 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[C:5]([F:9])=[CH:4][N:3]=1.[CH3:10][C:11]1[CH:17]=[CH:16][C:14]([NH2:15])=[CH:13][C:12]=1[C:18]([F:21])([F:20])[F:19]>>[Cl:1][C:2]1[N:7]=[C:6]([NH:15][C:14]2[CH:16]=[CH:17][C:11]([CH3:10])=[C:12]([C:18]([F:19])([F:20])[F:21])[CH:13]=2)[C:5]([F:9])=[CH:4][N:3]=1

Participants

3

Reactant 2

HCID 2507052,4-Dichloro-5-fluoropyrimidineHCID 27377154-Methyl-3-(trifluoromethyl)aniline

Product 1

HCID 220605602-chloro-5-fluoro-N4-(4-methyl-3-trifluoromethylphenyl)-4-pyrimidineamine

Procedure

In a like manner to the preparation of 2-chloro-N4-(3,4-ethylenedioxyphenyl)-5-fluoro-4-pyrimidineamine, 2,4-dichloro-5-fluoropyrimidine and 4-methyl-3-trifluoromethylaniline were reacted to provide 2-chloro-5-fluoro-N4-(4-methyl-3-trifluoromethylphenyl)-4-pyrimidineamine. 1H NMR (CDCl3): δ 8.10 (d, 1H, J=3.0 Hz), 7.85-7.78 (m, 2H), 7.33 (d, 1H, J=9.3 Hz), 6.96 (bs, 1H), 2.48 (d, 3H, J=1.2 Hz); 19F NMR (282 MHz, CDCl3): −17641, −44541; LCMS: purity: 97%; MS (m/e): 306 (MH+).

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-f79c714c6c3c4313adfa8c98d1b15921
Source dataset
uspto-grants-2014_09
Patent number
US08835430B2

Reaction notes

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