N4-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-(3-hydroxyphenyl)-2,4-primidinediamine → N2-(4-tert-butylphenyl)-5-fluoro-N2-[2,3-dihydro-2-(methoxycarbonyl)benzofuran-5-yl]-2,4-pyrimidinediamine
Reaction equation
C1COC2C=CC([NH:11][C:12]3[C:17]([F:18])=[CH:16][N:15]=[C:14]([NH:19][C:20]4[CH:25]=[CH:24][CH:23]=[C:22](O)[CH:21]=4)[N:13]=3)=CC=2O1.[C:27]([C:31]1[CH:36]=[CH:35][C:34](NC2C(F)=CN=C(Cl)N=2)=[CH:33][CH:32]=1)([CH3:30])([CH3:29])[CH3:28].NC1C=CC2[O:54][CH:53]([C:55]([O:57][CH3:58])=[O:56])[CH2:52]C=2C=1>>[C:27]([C:31]1[CH:32]=[CH:33][C:34]([N:19]([C:20]2[CH:25]=[CH:24][C:23]3[O:54][CH:53]([C:55]([O:57][CH3:58])=[O:56])[CH2:52][C:22]=3[CH:21]=2)[C:14]2[N:13]=[C:12]([NH2:11])[C:17]([F:18])=[CH:16][N:15]=2)=[CH:35][CH:36]=1)([CH3:28])([CH3:29])[CH3:30]Participants
4
Reactant 3
Product 1
Procedure
In a manner similar to the preparation of N4-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-(3-hydroxyphenyl)-2,4-pyrimidinediamine, N4-(4-tert-butylphenyl]-2-chloro-5-fluoro-4-pyrimidineamine and 5-amino-2,3-dihydro-2-(methoxycarbonyl)benzofuran were reacted to yield N2-(4-tert-butylphenyl)-5-fluoro-N2-[2,3-dihydro-2-(methoxycarbonyl)benzofuran-5-yl]-2,4-pyrimidinediamine. 1H NMR (DMSO-d6): δ 10.16 (bs, 1H), 9.84 (bs, 1H), 8.16 (d, 1H, J=5.4 Hz), 7.56 (d, 2H, J=8.1 Hz), 7.49 (s, 1H), 7.35 (d, 2H, J=8.7 Hz), 7.13 (dd, 1H, J=1.8 and 8.7 Hz), 6.78 (d, 1H, J=8.7 Hz), 5.35 (dd, 1H, J=6.6 and 10.5 Hz), 3.52 (dd, 1H, J=10.5 and 16.5 Hz), 3.20 (dd, 1H, J=6.6 and 16.5 Hz), 1.27 (s, 9H); LCMS: ret. time: 26.52 min.; purity: 96%; MS (m/e): 437 (MH+).
Workup
- customwere reacted
Sources & evidence
- ORD record
- ord-04acfd73afa747e789ad8b88365c1aa6
- Source dataset
- uspto-grants-2016_08
- Patent number
- US09416112B2
Reaction notes
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