4-Aminobenzonitrile → N2,N4-bis(4-cyanophenyl)-5-fluoro-2,4-pyrimidinediamine

HRID 1483356Notes

Reaction equation

[NH2:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1.Cl[C:11]1[N:16]=[C:15](Cl)[C:14]([F:18])=[CH:13][N:12]=1>>[C:6]([C:5]1[CH:8]=[CH:9][C:2]([NH:1][C:11]2[N:16]=[C:15]([NH:1][C:2]3[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=3)[C:14]([F:18])=[CH:13][N:12]=2)=[CH:3][CH:4]=1)#[N:7]

Participants

Reactant 2

HCID 133964-Aminobenzonitrile

HCID 2507052,4-Dichloro-5-fluoropyrimidine

Product 1

HCID 15603964N2,N4-bis(4-cyanophenyl)-5-fluoro-2,4-pyrimidinediamine

Procedure

In like manner to the preparation of N2,N4-bis(3-hydroxyphenyl)-5-fluoro-4-pyrimidineamine, 4-aminobenzonitrile and 2,4-dichloro-5-fluoropyrimidine gave N2,N4-bis(4-cyanophenyl)-5-fluoro-2,4-pyrimidinediamine. 1H NMR (DMSO-d6): δ 7.26 (d, J=8.7 Hz, 2H), 7.36 (d, J=9.0 Hz, 2H), 7.43 (d, J=8.7 Hz, 2H), 7.60 (d, J=8.7 Hz, 2H), 7.86 (d, J=3.6 Hz, 1H), 9.49 (br, 1H, NH), 9.51 (br, 1H, NH); 19F NMR (282 MHz, DMSO-d6): δ −161.48; LC: 27.15 min.; 100%; MS (m/e): 331.00 (MH+).

Sources & evidence

ORD record: ord-5193b19bb173415cb6593db34082042f
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09416112B2

Reaction notes

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