P-Anisidine → 5-fluoro-N,N'-bis(4-methoxyphenyl)pyrimidine-2,4-diamine

HRID 1829269Notes

Reaction equation

HRID 1829269 reaction equation
Cl[C:2]1[N:7]=[C:6](Cl)[C:5]([F:9])=[CH:4][N:3]=1.[CH3:10][O:11][C:12]1[CH:18]=[CH:17][C:15]([NH2:16])=[CH:14][CH:13]=1>>[CH3:10][O:11][C:12]1[CH:18]=[CH:17][C:15]([NH:16][C:2]2[N:7]=[C:6]([NH:16][C:15]3[CH:17]=[CH:18][C:12]([O:11][CH3:10])=[CH:13][CH:14]=3)[C:5]([F:9])=[CH:4][N:3]=2)=[CH:14][CH:13]=1

Participants

3

Reactant 2

HCID 7732P-AnisidineHCID 2507052,4-Dichloro-5-fluoropyrimidine

Product 1

HCID 8029425-fluoro-N,N'-bis(4-methoxyphenyl)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-methoxyaniline were reacted to yield N2,N4-bis(4-methoxyphenyl)-5-fluoro-2,4-pyrimidinediamine. 1H NMR (CD3OD): δ 7.67 (d, 1H, J=4.8 Hz), 7.43 (d, 2H, J=9.3 Hz), 7.67 (d, 2H, J=8.7 Hz), 6.87 (d, 2H, J=9.6 Hz), 6.83 (d, 2H, J=8.7 Hz), 3.83 (s, 3H), 3.81(s, 3H); LCMS: ret. time: 22.53 min.; purity: 100%; MS (m/e): 341 (MH+).

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-9aaea7b3e3a040098cfdb0cd051f5bac
Source dataset
uspto-grants-2006_06
Patent number
US07060827B2

Reaction notes

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