Methyl iodide → HCID 136367426, compound

HRID 252640Notes

Reaction equation

[NH2:1][C:2]1[CH:22]=[CH:21][C:5]([O:6][C:7]2[C:12]([C:13]3[CH:18]=[CH:17][N:16]=[C:15]([NH:19][CH3:20])[N:14]=3)=[CH:11][CH:10]=[CH:9][N:8]=2)=[CH:4][CH:3]=1.[C:23]([N:31]=[C:32]=[S:33])(=[O:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.I[CH3:35]>CC(C)=O>[C:23]([NH:31][C:32](=[N:1][C:2]1[CH:22]=[CH:21][C:5]([O:6][C:7]2[C:12]([C:13]3[CH:18]=[CH:17][N:16]=[C:15]([NH:19][CH3:20])[N:14]=3)=[CH:11][CH:10]=[CH:9][N:8]=2)=[CH:4][CH:3]=1)[S:33][CH3:35])(=[O:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a heterogeneous brown mixture of 4-(2-(4-aminophenoxy)pyridin-3-yl)-N-methylpyrimidin-2-amine (0.260 g, 0.886 mmol) in 2 mL acetone was added benzoyl isothiocyanate (0.136 ml, 0.975 mmol) dropwise via syringe. The mixture became homogeneous and remained brown. After 10 min, a precip formed. After 16 h, iodomethane (0.0554 ml, 0.886 mmol) was added, and the reaction was heated to 80° C. The mixture became homogeneous. After 3 h, further iodomethane (0.0554 ml, 0.886 mmol) was added and after 1 h at 80° C. and 3 days at ambient temperature, the reaction was adsorbed onto 1.7 g SiO2 and dried. The solid was purified by silica gel chromatography, 40 g, 0-10% MeOH/MC, to give 1-benzoyl-2-methyl-3-(4-(3-(2-(methylamino)pyrimidin-4-yl)pyridin-2-yloxy)phenyl)isothiourea which was used without further purification. MS m/z=471 [M+H]+. Calc'd for C25H22N6O2: 470.5.

Workup

customa precip formed
waitAfter 16 h
waitAfter 3 h
customdried
customThe solid was purified by silica gel chromatography, 40 g, 0-10% MeOH/MC

Sources & evidence

ORD record: ord-20cd295e0d6f410c9caeb5529c50727a
Source dataset: uspto-grants-2011_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07868177B2

Reaction notes

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