4-Amino-2,5-dimethylphenol → N2,N4-bis(2,5-dimethyl-4-hydroxyphenyl)-5-fluoro-2,4-pyrimidinediamine

HRID 76519

Reaction equation

HRID 76519 reaction equation
Cl[C:2]1[N:7]=[C:6](Cl)[C:5]([F:9])=[CH:4][N:3]=1.[CH3:10][C:11]1[CH:17]=[C:16]([OH:18])[C:15]([CH3:19])=[CH:14][C:12]=1[NH2:13]>>[CH3:10][C:11]1[CH:17]=[C:16]([OH:18])[C:15]([CH3:19])=[CH:14][C:12]=1[NH:13][C:2]1[N:7]=[C:6]([NH:13][C:12]2[CH:14]=[C:15]([CH3:19])[C:16]([OH:18])=[CH:17][C:11]=2[CH3:10])[C:5]([F:9])=[CH:4][N:3]=1

Participants

3

Reactant 2

HCID 765444-Amino-2,5-dimethylphenolHCID 2507052,4-Dichloro-5-fluoropyrimidine

Product 1

HCID 22060580N2,N4-bis(2,5-dimethyl-4-hydroxyphenyl)-5-fluoro-2,4-pyrimidinediamine

Procedure

In like manner to the preparation of N2,N4-bis(3-hydroxyphenyl)-5-fluoro-2,4-pyrimidinediamine, 2,4-dichloro-5-fluoropyrimidine and 2,5-dimethyl-4-hydroxyaniline were reacted to yield N2,N4-bis(2,5-dimethyl-4-hydroxyphenyl)-5-fluoro-2,4-pyrimidinediamine. 1H NMR (CD3OD): δ 7.63 (d, 1H, J=4.2 Hz), 7.05 (s, 1H), 6.97 (s, 1H), 6.64 (1H), 6.54 (s, 1H), 2.12 (s, 6H), 2.06 (s, 3H), 2.03 (s, 3H), 2.03 (s, 3H); 19F NMR (CD3OD): −48488; LCMS: ret. time: 18.28; purity; 94%; MS (m/e): 369 (MH+).

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-c9c4baac76e2401fa7eda020a3ea6550
Source dataset
uspto-grants-2014_09
Patent number
US08835430B2

Linked notes

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