(2-Chloro-5-fluoropyrimidin-4-yl)-(3,4-dichlorophenyl)amine → (+/-)-N4-(3,4-dichlorophenyl)-N2-(2,3-dihydro-2-methoxycarbonylbenzofuran-5-yl)-5-fluoro-2,4-pyrimidinediamine

HRID 1483556Notes

Reaction equation

HRID 1483556 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][CH:8]([C:10]([O:12][CH3:13])=[O:11])[CH2:7][C:6]=2[CH:14]=1.Cl[C:16]1[N:21]=[C:20]([NH:22][C:23]2[CH:28]=[CH:27][C:26]([Cl:29])=[C:25]([Cl:30])[CH:24]=2)[C:19]([F:31])=[CH:18][N:17]=1>>[Cl:30][C:25]1[CH:24]=[C:23]([NH:22][C:20]2[C:19]([F:31])=[CH:18][N:17]=[C:16]([NH:1][C:2]3[CH:3]=[CH:4][C:5]4[O:9][CH:8]([C:10]([O:12][CH3:13])=[O:11])[CH2:7][C:6]=4[CH:14]=3)[N:21]=2)[CH:28]=[CH:27][C:26]=1[Cl:29]

Participants

3

Reactant 2

HCID 22060411(2-Chloro-5-fluoropyrimidin-4-yl)-(3,4-dichlorophenyl)amineHCID 22060823Methyl 5-amino-2,3-dihydrobenzofuran-2-carboxylate

Product 1

HCID 10310474(+/-)-N4-(3,4-dichlorophenyl)-N2-(2,3-dihydro-2-methoxycarbonylbenzofuran-5-yl)-5-fluoro-2,4-pyrimidinediamine

Procedure

In like manner to the preparation of (±)-N4-(3,4-difluorophenyl)-N2-(2,3-dihydro-2-methoxycarbonylbenzofuran-5-yl)-5-fluoro-2,4-pyrimidinediamine, the reaction of (±)-5-amino-2,3-dihydro-2-methoxycarbonylbenzofuran with 2-chloro-N4-(3,4-dichlorophenyl)-5-fluoro-4-pyrimidineamine gave (±)-N4-(3,4-dichlorophenyl)-N2-(2,3-dihydro-2-methoxycarbonylbenzofuran-5-yl)-5-fluoro-2,4-pyrimidinediamine. 1H NMR (DMSO-d6): δ 10.13 (bs, 1H), 9.70 (bs, 1H), 8.21 (d, 1H, J=4.8 Hz), 8.04 (d, 1H, J=2.4 Hz), 7.68 (m, 1H), 7.54 (d, 1H, J=9.0 Hz), 7.37 (bs, 1H), 7.19 (m, 1H), 6.80 (d, 1H, J=8.7 Hz), 5.35 (dd, 1H, J=6.6 Hz), 3.69 (s, 3H), 3.53 (dd, 1H, J=10.5 and 11.1 Hz), 3.21 (dd, 1H, J=6.0 Hz); LCMS: purity: 100%; MS (m/e): 450 (MH+).

Workup

  1. customIn like manner to the preparation of (±)-N4-(3,4-difluorophenyl)-N2-(2,3-dihydro-2-methoxycarbonylbenzofuran-5-yl)-5-fluoro-2,4-pyrimidinediamine

Sources & evidence

ORD record
ord-e0c1f9f5f0844e01b3b58f83a764c777
Source dataset
uspto-grants-2016_08
Patent number
US09416112B2

Reaction notes

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