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

HRID 71379Notes

Reaction equation

HRID 71379 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.ClC1N=C(Cl)C=CN=1.OC1C=C(C=CC=1)N>>[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)[CH:12]=[CH:11][N:10]=2)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 115683-AminophenolHCID 775312,4-DichloropyrimidineHCID 9904854R-112

Product 1

HCID 10149490N2,N4-bis(3-hydroxyphenyl)-2,4-pyrimidinediamine

Procedure

In a manner analogous to the preparation of N2,N4-bis(3-hydroxyphenyl)-5-fluoro-2,4-pyrimidinediamine, the reaction of 2,4-dichloropyrimidine with 3-hydroxyaniline gave N2,N4-bis(3-hydroxyphenyl)-2,4-pyrimidinediamine. LCMS: ret. time: 16.21 min.; purity: 100%; MS (m/e): 295 (MH+).

Sources & evidence

ORD record
ord-49cb6853bfaa4fc7ab14e3ee828f54f4
Source dataset
uspto-grants-2014_09
Patent number
US08822685B2

Reaction notes

Loading…