Diphenyl Ether → 3,6-Dimethyl-2-(3-pyridinyl)thieno[2,3-b]pyridin-4-amine

HRID 573559Notes

Reaction equation

HRID 573559 reaction equation
[NH2:1][C:2]1[C:7](C(O)=O)=[C:6]([CH3:11])[N:5]=[C:4]2[S:12][C:13]([C:16]3[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=3)=[C:14]([CH3:15])[C:3]=12.C1(OC2C=CC=CC=2)C=CC=CC=1>>[CH3:15][C:14]1[C:3]2[C:2]([NH2:1])=[CH:7][C:6]([CH3:11])=[N:5][C:4]=2[S:12][C:13]=1[C:16]1[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=1

Participants

3

Reactant 2

HCID 7583Diphenyl EtherHCID 683238714-Amino-3,6-dimethyl-2-(3-pyridinyl)thieno[2,3-b]pyridine-5-carboxylic acid

Product 1

HCID 683237913,6-Dimethyl-2-(3-pyridinyl)thieno[2,3-b]pyridin-4-amineYield 53.9%

Conditions

Temperature
200 °C

Procedure

A mixture of 4-amino-3,6-dimethyl-2-(3-pyridinyl)thieno[2,3-b]pyridine-5-carboxylic acid (98 mg, 0.327 mmol) (Description 33) and diphenyl ether (2 mL) was heated at 200° C. for 2.5 h. After cooling to RT, the mixture was purified by chromatography on silica gel, eluting with a gradient of 0-100% ethyl acetate in cyclohexane then followed by 10% MeOH in DCM, to afford the title compound (45 mg). LCMS (A) m/z: 256 [M+1]+, Rt 0.61 min (acidic).

Workup

  1. temperatureAfter cooling to RT
  2. customthe mixture was purified by chromatography on silica gel
  3. washeluting with a gradient of 0-100% ethyl acetate in cyclohexane

Sources & evidence

ORD record
ord-00d19eeed68f4896875dfb1ca34d1f9d
Source dataset
uspto-grants-2015_05
Patent number
US09029545B2

Reaction notes

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