4-Ethylaniline → HCID 178435877, compound

HRID 733907Notes

Reaction equation

HRID 733907 reaction equation
[CH2:1]1[CH2:10][O:9][C:8]2[CH:7]=[CH:6][C:5]([NH:11][C:12]3[C:17]([F:18])=[CH:16][N:15]=[C:14]([NH:19]C4C=CC=C(O)C=4)[N:13]=3)=[CH:4][C:3]=2[O:2]1.ClC1N=C(NC2C=CC3OCCOC=3C=2)C(F)=CN=1.[CH2:46]([C:48]1[CH:54]=[CH:53][C:51](N)=[CH:50][CH:49]=1)[CH3:47]>>[CH2:1]1[CH2:10][O:9][C:8]2[CH:7]=[CH:6][C:5]([NH:11][C:12]3[C:17]([F:18])=[CH:16][NH:15][C:14]([C:51]4[CH:53]=[CH:54][C:48]([CH2:46][CH3:47])=[CH:49][CH:50]=4)([NH2:19])[N:13]=3)=[CH:4][C:3]=2[O:2]1

Participants

4

Reactant 3

HCID 115044-EthylanilineHCID 22060334N4-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-(3-hydroxyphenyl)-2,4-primidinediamineHCID 220603622-chloro-5-fluoro-N-(3,4-ethylenedioxyphenyl)-4-pyrimidineamine

Product 1

HCID 178435877HCID 178435877, compound

Procedure

In a manner similar to the preparation of N4-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-(3-hydroxyphenyl)-2,4-pyrimidinediamine, 2-chloro-N4-(3,4-ethylenedioxyphenyl)-5-fluoro-4-pyrimidineamine and 4-ethylaniline were reacted to yield N4-(3,4-ethylenedioxyphenyl)-2-(4-ethylphenyl)-5-fluoro-2,4-pyrimidinediamine. 1H NMR (CDCl3): δ 7.87 (bs, 1H), 7.42 (d, 2H, J=8.7 Hz), 7.26 (d, 1H, J=3.0 Hz), 7.13–7.08 (m, 3H), 6.95 (dd, 1H, J=2.4 and 8.7 Hz), 6.82 (d, 1H, J=9.0 Hz), 6.60 (bs, 1H), 4.23 (s, 4H), 2.59 (q, 2H, J=7.5 Hz), 1.20 (t, 3H, J=7.5 Hz); 19F NMR (CDCl3): −47549; LCMS: ret. time: 25.31 min.; purity: 99%; MS (m/e): 367 (MH+).

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-72d385c578cb48d59b443205f7eac1cd
Source dataset
uspto-grants-2009_09
Patent number
US07589200B2

Reaction notes

Loading…