3-Methoxyaniline → N2,N4-bis(3-methoxyphenyl)-5-fluoro-2,4-pyrimidinediamine

HRID 2277866Notes

Reaction equation

HRID 2277866 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:13]=[C:14]([CH:16]=[CH:17][CH:18]=1)[NH2:15]>>[CH3:10][O:11][C:12]1[CH:13]=[C:14]([NH:15][C:2]2[N:7]=[C:6]([NH:15][C:14]3[CH:16]=[CH:17][CH:18]=[C:12]([O:11][CH3:10])[CH:13]=3)[C:5]([F:9])=[CH:4][N:3]=2)[CH:16]=[CH:17][CH:18]=1

Participants

3

Reactant 2

HCID 108243-MethoxyanilineHCID 2507052,4-Dichloro-5-fluoropyrimidine

Product 1

HCID 22061080N2,N4-bis(3-methoxyphenyl)-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 3-methoxyaniline were reacted to yield N2,N4-bis(3-methoxyphenyl)-5-fluoro-2,4-pyrimidinediamine. 1H NMR (CD3OD): δ 7.96 (d, 1H, J=5.4 Hz), 7.24 (m, 6H), 7.06 (t, 1H, J=2.4 Hz), 7.00 (dt, 1H, J=1.2 Hz), 6.79 (m, 1H), 3.72 (s, 3H), 3.70 (s, 3H); 19F NMR (CD3OD): δ −46112; LCMS: ret. time: 23.46 min.; purity: 99%; MS (m/e): 341 (MH+).

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-be22145529834bc292dfd2cc2cc4856a
Source dataset
uspto-grants-2015_09
Patent number
US09133133B2

Reaction notes

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