4-Fluoroaniline → 5-fluoro-N,N'-bis(4-fluorophenyl)pyrimidine-2,4-diamine

HRID 1724320Notes

Reaction equation

HRID 1724320 reaction equation
Cl[C:2]1[N:7]=[C:6](Cl)[C:5]([F:9])=[CH:4][N:3]=1.[F:10][C:11]1[CH:17]=[CH:16][C:14]([NH2:15])=[CH:13][CH:12]=1>>[F:10][C:11]1[CH:17]=[CH:16][C:14]([NH:15][C:2]2[N:7]=[C:6]([NH:15][C:14]3[CH:16]=[CH:17][C:11]([F:10])=[CH:12][CH:13]=3)[C:5]([F:9])=[CH:4][N:3]=2)=[CH:13][CH:12]=1

Participants

3

Reactant 2

HCID 97314-FluoroanilineHCID 2507052,4-Dichloro-5-fluoropyrimidine

Product 1

HCID 9543085-fluoro-N,N'-bis(4-fluorophenyl)pyrimidine-2,4-diamine

Procedure

In like manner to the preparation of N2,N4-bis(3-hydroxyphenyl)-5-fluoro-2,4-pyrimidinediamine, 2,4-dichloro-5-fluoropyrimidine and 4-fluoroaniline were reacted to yield N2,N4-bis(4-fluorophenyl)-5-fluoro-2,4-pyrimidinediamine. 1H NMR (CDCl3): δ 8.79 (d, 2H, J=5.4 Hz), 7.40 (m, 2H), 7.30 (m, 2H), 6.90 (m, 4H); 19NMR (CDCl3): −32425 (s, 1F), −32940 (s, 1F), −45525 (s, 1F); LCMS: ret. time: 23.53 min.; purity: 100%; MS (m/e): 317 (MH+).

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-c95361369fbc42d991e83af47265c841
Source dataset
uspto-grants-2009_02
Patent number
US07485724B2

Reaction notes

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