p-Toluidine → 5-fluoro-N,N'-bis(4-methylphenyl)pyrimidine-2,4-diamine

HRID 1474840Notes

Reaction equation

HRID 1474840 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]=[CH:16][C:14]([NH2:15])=[CH:13][CH:12]=1>>[CH3:10][C:11]1[CH:17]=[CH:16][C:14]([NH:15][C:2]2[N:7]=[C:6]([NH:15][C:14]3[CH:16]=[CH:17][C:11]([CH3:10])=[CH:12][CH:13]=3)[C:5]([F:9])=[CH:4][N:3]=2)=[CH:13][CH:12]=1

Participants

3

Reactant 2

HCID 7813p-ToluidineHCID 2507052,4-Dichloro-5-fluoropyrimidine

Product 1

HCID 220609895-fluoro-N,N'-bis(4-methylphenyl)pyrimidine-2,4-diamine

Procedure

In like manner to the preparation of N2,N4-bis(3-hydroxyphenyl)-5-fluoro-2,4-pyrimidinediamine, 2,4-dichloro-5-fluoropyrimidine and 4-methylaniline were reacted to yield N2,N4-bis(4-methylphenyl)-5-fluoro-2,4-pyrimidinediamine. 1H NMR (CDCl3): δ 7.73 (d, 1H, J=4.2 Hz), 7.43 (d, 2H, J=8.1 Hz), 7.36 (d, 2H, J=8.4 Hz), 7.14 (d, 2H, J=8.4 Hz), 7.10 (d, 2H, J=8.1 Hz), 2.39 (s, 3H), 2.35 (s, 3H); LCMS: ret. time: 25.81 min.; purity: 99.65%; MS (m/e): 309 (MH+).

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-75149ff76781435fbbd38bf2431783fd
Source dataset
uspto-grants-2015_04
Patent number
US09018204B1

Reaction notes

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