Hydrochloric Acid → HCID 22594089, compound

HRID 1760982Notes

Reaction equation

HRID 1760982 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:14]=[C:13]([NH:15][C:16]([C:18]3[C:23]4[O:24][C:25]5[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=5[C:22]=4[CH:21]=[CH:20][CH:19]=3)=[O:17])[CH:12]=[CH:11][C:10]=2[CH3:31])[CH:5]=[CH:4][N:3]=1.[CH3:32][OH:33].Cl>C(OCC)C>[CH:21]1[C:22]2[C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=3[O:24][C:23]=2[C:18]([C:16]([NH:15][C:13]2[CH:12]=[CH:11][C:10]([CH3:31])=[C:9]([CH:14]=2)[NH:8][C:6]2[CH:5]=[CH:4][N:3]=[C:2]([O:33][CH3:32])[N:7]=2)=[O:17])=[CH:19][CH:20]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 225940952-Chloro-4-[5-(4-dibenzofuranylcarbonylamino)-2-methylanilino]pyrimidine

Product 1

HCID 22594089HCID 22594089, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 2-chloro-4-[5-(4-dibenzofuranylcarbonylamino)-2-methylanilino]pyrimidine (0.1 g), methanol (2 ml) and a 2M solution of hydrogen chloride in diethyl ether (0.5 ml) was stirred and heated to 70° C. for 24 hours. The reaction was evaporated and the residue was purified by column chromatography on silica using a 9:1 mixture of methylene chloride and methanol as eluent. There was thus obtained the title compound as a solid (0.025 g); NMR Spectrum: (DMSOd6) 2.26 (s, 3H), 3.85 (s, 3H), 6.36 (d, 1H), 7.34 (m, 1H), 7.46-7.7 (m, 4H), 7.87 (m, 1H), 7.92 (m, 1H), 8.01 (s, 1H), 8.09 (d, 1H), 8.29 (d, 1H), 8.4 (d, 1H), 9.09 (s, 1H), 10.46 (s, 1H); Mass Spectrum: M+H+ 425.

Workup

  1. customThe reaction was evaporated
  2. customthe residue was purified by column chromatography on silica using
  3. additiona 9:1 mixture of methylene chloride and methanol as eluent

Sources & evidence

ORD record
ord-fdb15dd81e784e25920aaed31ebf2d42
Source dataset
uspto-grants-2005_01
Patent number
US06846827B1

Reaction notes

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