Methyl iodide → 2-Methyl-6-(methyloxy)-3-[3-(methyloxy)phenyl]thieno[2,3-b]pyridin-4-amine

HRID 573562Notes

Reaction equation

[NH2:1][C:2]1[C:3]2[C:11]([C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH3:19])[CH:13]=3)=[C:10]([CH3:20])[S:9][C:4]=2[NH:5][C:6](=[O:8])[CH:7]=1.[C:21](=O)([O-])[O-].[K+].[K+].CI>CN(C=O)C>[CH3:20][C:10]1[S:9][C:4]2[N:5]=[C:6]([O:8][CH3:21])[CH:7]=[C:2]([NH2:1])[C:3]=2[C:11]=1[C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH3:19])[CH:13]=1

Participants

Conditions

Temperature: 90 °C

Procedure

To a suspension of 4-amino-2-methyl-3-[3-(methyloxy)phenyl]thieno[2,3-b]pyridin-6(7H)-one (Description 36) (120 mg, 0.419 mmol) in DMF (3 mL) was added potassium carbonate (116 mg, 0.838 mmol) and methyl iodide (0.029 mL, 0.461 mmol). The suspension was then heated to 90° C. under nitrogen atmosphere for ca. 2 hand then cooled to RT, quenched with water (ca. 25 mL) and extracted with ethyl acetate (ca. 25 mL×2). The combined organic layers were passed through a phase separator and solvent concentrated in vacuo. The residue was purified by normal phase chromatography, eluting with a gradient of 0-100% ethyl acetate in DCM followed by 0-20% MeOH in DCM, to afford the title compound (16.5 mg). LCMS (A) m/z: 301 [M+1]+, Rt 1.21 min (acidic).

Workup

temperaturethen cooled to RT
customquenched with water (ca. 25 mL)
extractionextracted with ethyl acetate (ca. 25 mL×2)
concentrationconcentrated in vacuo
customThe residue was purified by normal phase chromatography
washeluting with a gradient of 0-100% ethyl acetate in DCM

Sources & evidence

ORD record: ord-ac98575473d0415792aef8c2702d2b2e
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09029545B2

Reaction notes

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