Triethylamine → HCID 58629071, compound

HRID 1678048Notes

Reaction equation

HRID 1678048 reaction equation
Cl[C:2]1[C:3]2[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[S:8][C:4]=2[N:5]=[CH:6][N:7]=1.Cl.[CH3:15][O:16][C:17]1[CH:22]=[CH:21][C:20]([CH:23]([NH2:25])[CH3:24])=[CH:19][CH:18]=1.C(N(CC)CC)C>CN(C=O)C.O>[CH3:15][O:16][C:17]1[CH:22]=[CH:21][C:20]([CH:23]([NH:25][C:2]2[C:3]3[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[S:8][C:4]=3[N:5]=[CH:6][N:7]=2)[CH3:24])=[CH:19][CH:18]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 1222526256844-13-4HCID 17938752HCID 17938752, compound

Product 1

HCID 58629071HCID 58629071, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-chloro-6-nitrothieno[2,3-d]pyrimidine (prepared as disclosed in Bull. Chim. Soc. Fr. 1975, 3-4, Pt. 2, 592) (500 mg, 2.3 mmol), 1-(4-methoxyphenyl)ethanamine HCl (513 mg, 2.8 mmol), and triethylamine (581 mg, 5.7 mmol) in DMF (7 mL) was allowed to react for 24 hours at 20° C. The reaction mixture was diluted with water and extracted thrice into Et2O. The organic portions were combined, washed with brine, and dried (Na2SO4). The mixture was filtered through silica gel, and the solvent was removed in vacuo. The residue was purified by flash chromatography (40 percent EtOAc in pentane), yielding 385 mg.

Workup

  1. customto react for 24 hours at 20° C
  2. extractionextracted thrice into Et2O
  3. washwashed with brine
  4. dry with materialdried (Na2SO4)
  5. filtrationThe mixture was filtered through silica gel
  6. customthe solvent was removed in vacuo
  7. customThe residue was purified by flash chromatography (40 percent EtOAc in pentane)
  8. customyielding 385 mg

Sources & evidence

ORD record
ord-868f58824ea64c278a1c9a23750d7c16
Source dataset
uspto-grants-2011_08
Patent number
US08008487B2

Reaction notes

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