3-Chloroaniline → N,N'-bis(3-chlorophenyl)-5-fluoropyrimidine-2,4-diamine

HRID 1753361Notes

Reaction equation

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

Participants

Reactant 2

HCID 79323-Chloroaniline

HCID 2507052,4-Dichloro-5-fluoropyrimidine

Product 1

HCID 745199N,N'-bis(3-chlorophenyl)-5-fluoropyrimidine-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 3-chloroaniline were reacted to yield N2,N4-bis(3-chlorophenyl)-5-fluoro-2,4-pyrimidinediamine. 1H NMR (CD3OD): δ 8.08 (d, 1H, J=5.4 Hz), 7.70 (t, 1H, J=1.8 Hz), 7.57 (t, 1H, J=1.2 Hz), 7.54 (m, 1H), 7.35 (m, 4H), 7.28 (t, 1H, J=1.8 Hz), 7.24 (m, 1H), 7.22 (t, 1H, J=1.8 Hz); 19F NMR (CD3OD): −43631; LCMS: ret. time: 28.99 min.; purity: 99%; MS (m/e): 349 (M+).

Workup

customwere reacted

Sources & evidence

ORD record: ord-7453fcd360c444b5aaf7640e36bc47f1
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09162989B2

Reaction notes

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