3-Aminophenol → N2,N4-bis(3-hydroxyphenyl)-5-bromo-2,4-pyrimidinediamine

HRID 1753394Notes

Reaction equation

[OH:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[N:14]=[C:13]([NH:15][C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([OH:22])[CH:17]=3)[C:12](F)=[CH:11][N:10]=2)[CH:5]=[CH:6][CH:7]=1.[Br:24]C1C(Cl)=NC(Cl)=NC=1.NC1C=C(O)C=CC=1>>[OH:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[N:14]=[C:13]([NH:15][C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([OH:22])[CH:17]=3)[C:12]([Br:24])=[CH:11][N:10]=2)[CH:5]=[CH:6][CH:7]=1

Participants

Reactant 3

HCID 115683-Aminophenol

HCID 2899735-Bromo-2,4-dichloropyrimidine

HCID 9904854R-112

Product 1

HCID 22061141N2,N4-bis(3-hydroxyphenyl)-5-bromo-2,4-pyrimidinediamine

Procedure

In a manner similar to the preparation of N2,N4-bis(3-hydroxyphenyl)-5-fluoro-2,4-pyrimidinediamine, 5-bromo-2,4-dichloropyrimidine and 3-aminophenol were reacted to yield N2,N4-bis(3-hydroxyphenyl)-5-bromo-2,4-pyrimidinediamine. 1H NMR (DMSO-d6): δ 9.99 (bs, 1H), 9.34 (bs, 1H), 8.30 (s, 1H), 7.15 (t, 1H, J=8.4 Hz), 7.06-6.97 (m, 2H), 6.94-6.92 (m, 2H), 6.80 (bs, 1H), 6.62 (s, 1H, J=8.1 Hz), 6.43 (d, 1H, J=7.8 Hz); LCMS: ret. time: 18.48 min.; purity: 97%; MS (m/e): 374 (MH+).

Workup

customwere reacted

Sources & evidence

ORD record: ord-a80c3371e19b4945a29d1ede122d06ec
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09162989B2

Reaction notes

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