Pyridine → HCID 22674401, compound

HRID 1005721Notes

Reaction equation

HRID 1005721 reaction equation
[NH2:1][C:2]1[N:3]=[C:4]([C:11]([C:13]2[S:14][CH:15]=[CH:16][CH:17]=2)=[O:12])[C:5]2[S:10][CH:9]=[CH:8][C:6]=2[N:7]=1.N1C=CC=CC=1.[C:24](Cl)(=[O:26])[CH3:25]>O>[S:14]1[CH:15]=[CH:16][CH:17]=[C:13]1[C:11]([C:4]1[C:5]2[S:10][CH:9]=[CH:8][C:6]=2[N:7]=[C:2]([NH:1][C:24](=[O:26])[CH3:25])[N:3]=1)=[O:12]

Participants

5

Reactant 3

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 9903342HCID 9903342, compound

Product 1

HCID 22674401HCID 22674401, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2-aminothieno[3,2-d]pyrimidin-4-yl 2-thienylmethanone (0.07 g, 0.27 mmol), anhydrous pyridine (3 mL) and acetyl chloride (0.15 g, 1.88 mmol) was refluxed for 24 h, cooled to room temperature, poured into water (30 mL) and extracted with EtOAc (2×30 mL). The organic phase was washed with 1-M HCl (2×25 mL) and saturated brine (25 mL), dried (MgSO4) and concentrated in vacuo to give a yellow solid which was purified by chromatography (SiO2; heptane-EtOAc (2:1)] to give the title compound (50 mg, 58%) as a yellow solid.

Workup

  1. temperaturewas refluxed for 24 h
  2. extractionextracted with EtOAc (2×30 mL)
  3. washThe organic phase was washed with 1-M HCl (2×25 mL) and saturated brine (25 mL)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customto give a yellow solid which
  7. customwas purified by chromatography (SiO2

Sources & evidence

ORD record
ord-5230a7356b72453ca4574282627f84ab
Source dataset
uspto-grants-2004_09
Patent number
US06787541B1

Reaction notes

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