3-Aminophenol → 3-Hydroxyphenyl-5-cyano-2,4-pyrimidinediamine

HRID 76508Notes

Reaction equation

OC1C=C([NH:8][C:9]2[N:14]=[C:13]([NH:15]C3C=CC=C(O)C=3)[C:12](F)=[CH:11][N:10]=2)C=CC=1.Cl[C:25]1N=C(Cl)C(C#N)=C[N:26]=1.[OH:34][C:35]1[CH:36]=[C:37]([CH:39]=[CH:40][CH:41]=1)N>>[OH:34][C:35]1[CH:36]=[C:37]([C:11]2[N:10]=[C:9]([NH2:8])[N:14]=[C:13]([NH2:15])[C:12]=2[C:25]#[N:26])[CH:39]=[CH:40][CH:41]=1

Participants

Reactant 3

HCID 115683-Aminophenol

HCID 9904854R-112

HCID 140269072,4-Dichloro-5-cyanopyrimidine

Product 1

HCID 865911253-Hydroxyphenyl-5-cyano-2,4-pyrimidinediamine

Procedure

In a manner similar to the preparation of N2,N4-bis(3-hydroxyphenyl)-5-fluoro-2,4-pyrimidinediamine, 2,4-dichloro-5-cyanopyrimidine and 3-hydroxyaniline were reacted to yield N2,N4-bis(3-hydroxyphenyl-5-cyano-2,4-pyrimidinediamine. 1H NMR (DMSO-d6): δ 9.73 (bs, 1H), 9.40 (s, 1H), 9.33 (bs, 1H), 9.24 (s, 1H), 8.47 (s, 1H), 7.20 (d, 1H, J=7.5 Hz), 7.11 (t, 1H, J=7.5 Hz), 7.09-7.02 (m, 2H), 6.99-6.89 (m, 3H), 6.54 (d, 1H, J=7.2 Hz), 6.37 (dd, 1H, J=1.8 and 8.4 Hz); LCMS: ret. time: 19.71 min.; purity: 97%; MS (m/e): 320 (MH+).

Workup

customwere reacted

Sources & evidence

ORD record: ord-18579669c3c843318bf2a93604770dea
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08835430B2

Reaction notes

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