2,4-Dichloropyrimidine → 2-Chloro-4-[5-(4-dibenzofuranylcarbonylamino)-2-methylanilino]pyrimidine

HRID 1760979Notes

Reaction equation

[NH2:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]([C:12]2[C:17]3[O:18][C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=4[C:16]=3[CH:15]=[CH:14][CH:13]=2)=[O:11])[CH:5]=[CH:6][C:7]=1[CH3:8].[Cl:25][C:26]1[N:31]=[C:30](Cl)[CH:29]=[CH:28][N:27]=1.C(N(CC)C(C)C)(C)C>C(O)CCC>[Cl:25][C:26]1[N:31]=[C:30]([NH:1][C:2]2[CH:3]=[C:4]([NH:9][C:10]([C:12]3[C:17]4[O:18][C:19]5[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=5[C:16]=4[CH:15]=[CH:14][CH:13]=3)=[O:11])[CH:5]=[CH:6][C:7]=2[CH3:8])[CH:29]=[CH:28][N:27]=1

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of N-(3-amino-4-methylphenyl)dibenzofuran-4-carboxamide (1.5 g), 2,4-dichloropyrimidine (1.4 g), N,N-di-isopropylethylamine (2.9 ml) and n-butanol (70 ml) was stirred and heated to 120° C. for 76 hours. The mixture was evaporated and the residue was purified by column chromatography on silica using increasingly polar mixtures of isohexane and ethyl acetate as eluent. The material so obtained was triturated under ethyl acetate. There was thus obtained the title compound (0.83 g); NMR Spectrum: (DMSOd6) 2.17 (s, 3H), 6.53 (d, 1H), 7.31 (d, 1H), 7.43-7.65 (m, 4H), 7.79 (m, 2H), 7.84 (d, 1H), 8.1 (d, 1H), 8.21 (d, 1H), 8.34 (d, 1H), 9.62 (s, 1H), 10.42 (s, 1H); Mass Spectrum: M+H+ 429 and 431.

Workup

customThe mixture was evaporated
customthe residue was purified by column chromatography on silica using
temperatureincreasingly polar mixtures of isohexane and ethyl acetate as eluent
customThe material so obtained
customwas triturated under ethyl acetate

Sources & evidence

ORD record: ord-9bb1c15789a9437cb8a0f7225513c74b
Source dataset: uspto-grants-2005_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06846827B1

Reaction notes

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