3-Chloro-4-methoxyaniline → N,N'-bis(3-chloro-4-methoxyphenyl)-5-fluoropyrimidine-2,4-diamine

HRID 76735

Reaction equation

HRID 76735 reaction equation
Cl[C:2]1[N:7]=[C:6](Cl)[C:5]([F:9])=[CH:4][N:3]=1.[Cl:10][C:11]1[CH:12]=[C:13]([CH:15]=[CH:16][C:17]=1[O:18][CH3:19])[NH2:14]>>[Cl:10][C:11]1[CH:12]=[C:13]([NH:14][C:2]2[N:7]=[C:6]([NH:14][C:13]3[CH:15]=[CH:16][C:17]([O:18][CH3:19])=[C:11]([Cl:10])[CH:12]=3)[C:5]([F:9])=[CH:4][N:3]=2)[CH:15]=[CH:16][C:17]=1[O:18][CH3:19]

Participants

3

Reactant 2

HCID 214413-Chloro-4-methoxyanilineHCID 2507052,4-Dichloro-5-fluoropyrimidine

Product 1

HCID 1266496N,N'-bis(3-chloro-4-methoxyphenyl)-5-fluoropyrimidine-2,4-diamine

Procedure

In a like manner to the preparation of N2,N4-bis(3-hydroxyphenyl)-5-fluoro-2,4-pyrimidinediamine, 2,4-dichloro-5-fluoropyrimidine and 3-chloro-4-methoxyaniline were reacted to provide N2,N4-Bis(3-chloro-4-methoxyphenyl)-5-fluoro-2,4-pyrimidinediamine. 1H NMR (DMSO-d6): δ 9.90 (bs, 1H), 9.68 (bs, 1H), 8.16 (d, 1H, J=4.8 Hz), 7.72 (d, 1H, J=2.4 Hz), 7.65 (d, 1H, J=2.1 Hz), 7.58 (dd, 1H, J=2.4 and 9.0 Hz), 7.38 (dd, 1H, J=2.7 and 9.3 Hz), 7.12 (d, 1H, J=8.7 Hz), 7.12 (d, 1H, J=8.7 Hz), 7.05 (d, 1H, J=8.7 Hz), 3.83 (s, 3H), 3.79 (s, 3H); LCMS: purity: 99%; MS (m/e): 410 (MH+).

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-0c00ad0424914291853ae93f39340fae
Source dataset
uspto-grants-2014_09
Patent number
US08835430B2

Linked notes

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