Methanesulfonic Acid → HCID 22594096, compound

HRID 1760973Notes

Reaction equation

C([NH:4][C:5]1[N:10]=[C:9]([NH:11][C:12]2[CH:17]=[C:16]([NH:18][C:19]([C:21]3[CH:26]=[CH:25][N:24]=[C:23]([N:27]4[CH2:32][CH2:31][O:30][CH2:29][CH2:28]4)[CH:22]=3)=[O:20])[CH:15]=[CH:14][C:13]=2[CH3:33])[CH:8]=[CH:7][N:6]=1)C=C.CS(O)(=O)=O>CC(N(C)C)=O.[Pd]>[NH2:4][C:5]1[N:10]=[C:9]([NH:11][C:12]2[CH:17]=[C:16]([NH:18][C:19]([C:21]3[CH:26]=[CH:25][N:24]=[C:23]([N:27]4[CH2:28][CH2:29][O:30][CH2:31][CH2:32]4)[CH:22]=3)=[O:20])[CH:15]=[CH:14][C:13]=2[CH3:33])[CH:8]=[CH:7][N:6]=1

Participants

Conditions

Temperature: 140 °C

Procedure

A mixture of 2-allylamino-4-[2-methyl-5-(2-morpholinopyrid-4-ylcarbonylamino)anilino]pyrimidine (0.151 g), methanesulphonic acid (0.1 ml) and 30% palladium-on-carbon (0.034 g) in DMA (1 ml) was stirred and heated to 140° C. for 24 hours. The mixture was cooled to ambient temperature and filtered. A mixture of methylene chloride and isohexane was added to the filtrate. The resultant precipitate was isolated and purified by column chromatography on silica using a 89:10:1 mixture of methylene chloride, methanol and a saturated aqueous ammonium hydroxide solution as eluent. There was thus obtained the title compound as a solid (0.01 g); NMR Spectrum: (DMSOd6) 2.16 (s, 3H), 3.47 (m, 4H), 3.7 (m, 4H), 4.78 (br m, 4H), 5.98 (m, 1H), 7.01 (m, 1H), 7.16 (m, 2H), 7.39 (m, 1H), 7.65 (m, 1H), 7.72 (m, 1H), 8.17 (m, 1H); Mass Spectrum: M+H+ 406.

Workup

temperatureThe mixture was cooled to ambient temperature
filtrationfiltered
additionA mixture of methylene chloride and isohexane
additionwas added to the filtrate

Sources & evidence

ORD record: ord-86b2525bbded48f1bf47bc20143277f4
Source dataset: uspto-grants-2005_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06846827B1

Reaction notes

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