Phenylboronic Acid → N2,N4-bis(3-hydroxyphenyl)-5-phenyl-2,4-pyrimidinediamine

HRID 1753648Notes

Reaction equation

HRID 1753648 reaction equation
C1CO[C:8]2[CH:7]=[CH:6][C:5]([NH:11][C:12]3[N:17]=[C:16]([NH:18][C:19]4[CH:24]=[CH:23][C:22]5OCC[O:28][C:21]=5[CH:20]=4)[C:15]([C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)=[CH:14][N:13]=3)=[CH:4][C:3]=2[O:2]1.OC1C=C(NC2N=C(NC3C=CC=C(O)C=3)C(Br)=CN=2)C=CC=1.C1(B(O)O)C=CC=CC=1>>[OH:2][C:3]1[CH:4]=[C:5]([NH:11][C:12]2[N:17]=[C:16]([NH:18][C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([OH:28])[CH:20]=3)[C:15]([C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=3)=[CH:14][N:13]=2)[CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 3

HCID 66827Phenylboronic AcidHCID 22060379N2,N4-bis(3,4-ethylenedioxyphenyl)-5-phenyl-2,4-pyrimidinediamineHCID 22061141N2,N4-bis(3-hydroxyphenyl)-5-bromo-2,4-pyrimidinediamine

Product 1

HCID 22060237N2,N4-bis(3-hydroxyphenyl)-5-phenyl-2,4-pyrimidinediamine

Procedure

In a manner similar to the preparation of N2,N4-bis(3,4-ethylenedioxyphenyl)-5-phenyl-2,4-pyrimidinediamine, N2,N4-bis(3-hydroxyphenyl)-5-bromo-2,4-pyrimidinediamine and phenylboronic acid were reacted to yield N2,N4-bis(3-hydroxyphenyl)-5-phenyl-2,4-pyrimidinediamine. 1H NMR (CD3OD): δ 7.85 (bs, 1H), 7.54-7.38 (m, 5H), 7.13-7.11 (m, 2H). 7.10-7.04 (m, 3H), 6.97 (dt, 1H, J=1.8 and 8.1 Hz), 6.54 (ddd, 1H, J=1.9, 2.4, and 7.2 Hz), 6.44 (dt, 1H, J=1.8 and 6.0 Hz); LCMS: ret. time: 20.66 min.; purity: 96%; MS (m/e): 371 (MH+).

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-b4ba9e0519a24520a334c3c92df829fc
Source dataset
uspto-grants-2015_10
Patent number
US09162989B2

Reaction notes

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