2,4-Diaminopyrimidine → n4-(3,4-Ethylenedioxyphenyl)-5-fluoro-n2-(4-trifluoromethylthiophenyl)-2,4-pyrimidinediamine

HRID 734076Notes

Reaction equation

HRID 734076 reaction equation
N1C=CC(N)=NC=1N.Cl[C:10]1[N:15]=[C:14]([NH:16][C:17]2[CH:22]=[CH:21][C:20]3[O:23][CH2:24][CH2:25][O:26][C:19]=3[CH:18]=2)[C:13]([F:27])=[CH:12][N:11]=1.[F:28][C:29]([F:39])([F:38])[S:30][C:31]1[CH:37]=[CH:36][C:34]([NH2:35])=[CH:33][CH:32]=1>>[CH2:25]1[CH2:24][O:23][C:20]2[CH:21]=[CH:22][C:17]([NH:16][C:14]3[C:13]([F:27])=[CH:12][N:11]=[C:10]([NH:35][C:34]4[CH:36]=[CH:37][C:31]([S:30][C:29]([F:39])([F:28])[F:38])=[CH:32][CH:33]=4)[N:15]=3)=[CH:18][C:19]=2[O:26]1

Participants

4

Reactant 3

HCID 674312,4-DiaminopyrimidineHCID 1230544-((Trifluoromethyl)thio)anilineHCID 220603622-chloro-5-fluoro-N-(3,4-ethylenedioxyphenyl)-4-pyrimidineamine

Product 1

HCID 22060687n4-(3,4-Ethylenedioxyphenyl)-5-fluoro-n2-(4-trifluoromethylthiophenyl)-2,4-pyrimidinediamine

Procedure

In like manner to the preparation of 5-fluoro-N4-(3-hydroxyphenyl)-N2-[4-3-phenyl-1,2,4-oxadiazol-5-yl)methyleneoxyphenyl]-2,4-pyrimidinediamine, 2-chloro-N4-(3,4-ethylenedioxyphenyl)-5-fluoro-4-pyrimidineamine and 4-(trifluoromethylthio)aniline were reacted to provide N4-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-(4-trifluoromethylthiophenyl)-2,4-pyrimidinediamine. 1H NMR (DMSO-d6): δ 9.73 (s, 1H), 9.47 (s, 1H), 8.13 (d, 1H, J=3.6 Hz), 7.79 (d, 2H, J=9.0 Hz), 7.51 (d, 2H, J=9.0 Hz), 7.28 (d, 1H, J=2.1 Hz), 7.12 (dd, 1H, J=2.4 and 9.0 Hz), 6.83 (d, 1H, J=8.7 Hz), 4.23 (s, 4H); 19F NMR (282 MHz DMSO-d6): −12306; LCMS: purity: 97%; MS (m/e): 439(MH+).

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-ecf64a6b2775430d8e6a63a120ad3189
Source dataset
uspto-grants-2009_09
Patent number
US07589200B2

Reaction notes

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