Pyridine → HCID 22273539, compound

HRID 1064311Notes

Reaction equation

[CH3:1][S:2](Cl)(=[O:4])=[O:3].[CH3:6][N:7]1[C:11]([C:12]2[CH:17]=[CH:16][N:15]=[C:14]([NH:18][C:19]3[CH:24]=[CH:23][C:22]([NH2:25])=[CH:21][CH:20]=3)[N:13]=2)=[CH:10][N:9]=[C:8]1[CH3:26].N1C=CC=CC=1>C(Cl)Cl>[CH3:6][N:7]1[C:11]([C:12]2[CH:17]=[CH:16][N:15]=[C:14]([NH:18][C:19]3[CH:24]=[CH:23][C:22]([NH:25][S:2]([CH3:1])(=[O:4])=[O:3])=[CH:21][CH:20]=3)[N:13]=2)=[CH:10][N:9]=[C:8]1[CH3:26]

Participants

Conditions

Temperature: 4 °C

Procedure

Methanesulphonyl chloride (0.055 ml, 0.711 mmole) was added to a solution of 4-(1,2-dimethylimidazol-5-yl)-2-(4-aminoanilino)pyrimidine (Example 165; 0.18 g, 0.64 mmole) and pyridine (0.052 ml, 0.64 mmole) in DCM (2.0 mL) cooled at 4° C. The mixture was allowed to warm to ambient temperature. The mixture was partitioned between saturated aqueous sodium hydrogen carbonate solution and EtOAc. The organic layer was separated, the volatiles evaporated and the residue purified by column chromatography on silica gel eluting with DCM/7M methanolic ammonia (96:4) to give the title compound (0.15 g, 65%) as a solid. NMR: 2.36 (s, 3H), 2.90 (s, 3H), 3.91 (s, 3H), 7.06 (d, 1H), 7.14 (d, 2H), 7.57 (s, 1H), 7.64 (d, 2H), 8.33 (d, 1H), 9.37 (br s, 1H), 9.42 (s, 1H); m/z 359.

Workup

temperatureto warm to ambient temperature
customThe mixture was partitioned between saturated aqueous sodium hydrogen carbonate solution and EtOAc
customThe organic layer was separated
customthe volatiles evaporated
customthe residue purified by column chromatography on silica gel eluting with DCM/7M methanolic ammonia (96:4)

Sources & evidence

ORD record: ord-3743806dd52c41b39eb8857ce6f945b9
Source dataset: uspto-grants-2005_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06969714B2

Reaction notes

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