Dimethylformamide → 4-Amino-2,6-dimethylthieno[2,3-b]pyridine-3-carbonitrile

HRID 573597Notes

Reaction equation

HRID 573597 reaction equation
Br[C:2]1[C:10]2[C:9]([NH2:11])=[CH:8][C:7]([CH3:12])=[N:6][C:5]=2[S:4][C:3]=1[CH3:13].C(OCC)(=O)C.[CH3:20][N:21](C=O)C>[C-]#N.[Zn+2].[C-]#N.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[NH2:11][C:9]1[CH:8]=[C:7]([CH3:12])[N:6]=[C:5]2[S:4][C:3]([CH3:13])=[C:2]([C:20]#[N:21])[C:10]=12

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 8857Ethyl AcetateHCID 683238623-Bromo-2,6-dimethylthieno[2,3-b]pyridin-4-amine2×

Product 1

HCID 683240634-Amino-2,6-dimethylthieno[2,3-b]pyridine-3-carbonitrile

Reagents, catalysts & solvents 2

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 178418397HCID 178418397, compoundCatalyst

Conditions

Temperature
140 °C

Procedure

A mixture of 3-bromo-2,6-dimethylthieno[2,3-b]pyridin-4-amine (Description 8) (200 mg, 0.778 mmol), zinc cyanide (183 mg, 1.556 mmol) and tetrakis(triphenylphosphine)palladium(0) (90 mg, 0.078 mmol) in DMF (5 mL) was heated in a microwave at 140° C. for 1 h. Another batch of 3-bromo-2,6-dimethylthieno[2,3-b]pyridin-4-amine (200 mg, 0.778 mmol) was subjected to the same conditions. The mixtures were then combined and ethyl acetate (50 mL) added. The resulting mixture was washed with saturated NaHCO3 (20 mL) followed by brine (20 mL×2) and the organic layer dried over MgSO4, filtered and the solvent removed in vacuo. The residue was purified by normal phase chromatography, eluting with a gradient of 0-40% ethyl acetate in cyclohexane, to give the title compound (237.7 mg). LCMS (A) m/z: 204 [M+1]+, Rt 0.61 min (acidic).

Workup

  1. washThe resulting mixture was washed with saturated NaHCO3 (20 mL)
  2. dry with materialthe organic layer dried over MgSO4
  3. filtrationfiltered
  4. customthe solvent removed in vacuo
  5. customThe residue was purified by normal phase chromatography
  6. washeluting with a gradient of 0-40% ethyl acetate in cyclohexane

Sources & evidence

ORD record
ord-98aff5cbfb6845c4ae9ffd24de81a059
Source dataset
uspto-grants-2015_05
Patent number
US09029545B2

Reaction notes

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