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

Participants

Role	Name	HCID	Charge
Reactant	2,4-Diaminopyrimidine	HCID 67431	—
Reactant	4-((Trifluoromethyl)thio)aniline	HCID 123054	—
Reactant	2-chloro-5-fluoro-N-(3,4-ethylenedioxyphenyl)-4-pyrimidineamine	HCID 22060362	—
Product	n4-(3,4-Ethylenedioxyphenyl)-5-fluoro-n2-(4-trifluoromethylthiophenyl)-2,4-pyrimidinediamine	HCID 22060687	—

Reaction Steps

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+).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07589200B2
Source dataset	uspto-grants-2009_09
ORD ID	ord-ecf64a6b2775430d8e6a63a120ad3189
Source note	uspto-grants-2009_09