5-Methyl-3-phenyl-4-isoxazolamine → N4-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-(3-phenyl-5-methylisoxazol-4-yl)-2,4-pyrimidinediamine

HRID 1483407Notes

Reaction equation

HRID 1483407 reaction equation
C1COC2C=CC(NC3C(F)=CN=C(NC4C=CC=C(O)C=4)N=3)=CC=2O1.Cl[C:28]1[N:33]=[C:32]([NH:34][C:35]2[CH:40]=[CH:39][C:38]3[O:41][CH2:42][CH2:43][O:44][C:37]=3[CH:36]=2)[C:31]([F:45])=[CH:30][N:29]=1.[CH3:46][C:47]1[O:51][N:50]=[C:49]([C:52]2[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=2)[C:48]=1[NH2:58]>>[CH2:43]1[CH2:42][O:41][C:38]2[CH:39]=[CH:40][C:35]([NH:34][C:32]3[C:31]([F:45])=[CH:30][N:29]=[C:28]([NH:58][C:48]4[C:49]([C:52]5[CH:53]=[CH:54][CH:55]=[CH:56][CH:57]=5)=[N:50][O:51][C:47]=4[CH3:46])[N:33]=3)=[CH:36][C:37]=2[O:44]1

Participants

4

Reactant 3

HCID 27475845-Methyl-3-phenyl-4-isoxazolamineHCID 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 22060575N4-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-(3-phenyl-5-methylisoxazol-4-yl)-2,4-pyrimidinediamine

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 5-methyl-3-phenyl-4-isoxazolamine were reacted to yield N4-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-(3-phenyl-5-methylisoxazol-4-yl)-2,4-pyrimidinediamine. LCMS: ret. time: 20.90 min.; purity: 96%; MS (m/e): 420 (MH+).

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-a9c72af8f247415f8b7d55f92efb8f38
Source dataset
uspto-grants-2016_08
Patent number
US09416112B2

Reaction notes

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