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

Participants

Role	Name	HCID	Charge
Reactant	Phenylboronic Acid	HCID 66827	—
Reactant	N2,N4-bis(3,4-ethylenedioxyphenyl)-5-phenyl-2,4-pyrimidinediamine	HCID 22060379	—
Reactant	N2,N4-bis(3-hydroxyphenyl)-5-bromo-2,4-pyrimidinediamine	HCID 22061141	—
Product	N2,N4-bis(3-hydroxyphenyl)-5-phenyl-2,4-pyrimidinediamine	HCID 22060237	—

Reaction Steps

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+).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08822685B2
Source dataset	uspto-grants-2014_09
ORD ID	ord-0b16a8bffdb24876a26caa13f7b2de76
Source note	uspto-grants-2014_09