3-Aminobiphenyl → N2,N4-bis[(3-phenyl)phenyl]-5-fluoro-2,4-pyrimidinediamine

HRID 76482

Reaction equation

Cl[C:2]1[N:7]=[C:6](Cl)[C:5]([F:9])=[CH:4][N:3]=1.[C:10]1([C:16]2[CH:17]=[C:18]([CH:20]=[CH:21][CH:22]=2)[NH2:19])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>>[C:10]1([C:16]2[CH:17]=[C:18]([NH:19][C:2]3[N:7]=[C:6]([NH:19][C:18]4[CH:20]=[CH:21][CH:22]=[C:16]([C:10]5[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=5)[CH:17]=4)[C:5]([F:9])=[CH:4][N:3]=3)[CH:20]=[CH:21][CH:22]=2)[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

Reactant 2

HCID 167173-Aminobiphenyl

HCID 2507052,4-Dichloro-5-fluoropyrimidine

Product 1

HCID 66759549N2,N4-bis[(3-phenyl)phenyl]-5-fluoro-2,4-pyrimidinediamine

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-phenylaniline were reacted to yield N2,N4-bis[(3-phenyl)phenyl]-5-fluoro-2,4-pyrimidinediamine. 1H NMR (CD3OD): δ 8.02 (d, 1H, J=5.1 Hz), 7.82 (t, 1H, J=1.5 Hz), 7.67 (t, 1H, J=1.8 Hz), 7.58 (dd, 1H, J=1.2 and 7.2 Hz), 7.42-7.24 (m, 15H); LCMS: ret. time: 32.06 min.; purity: 94%; MS (m/e): 433 (MH+).

Workup

customwere reacted

Sources & evidence

ORD record: ord-c1b140d3bce04315a3393dc9f9a8d455
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08835430B2

Linked notes

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