Triethylamine → (5-Chlorothieno[2,3-d]pyrimidin-4-yl)-[1-(4-isopropylphenyl)ethyl]amine

HRID 1678047

Reaction equation

HRID 1678047 reaction equation
Cl[C:2]1[C:3]2[C:10]([Cl:11])=[CH:9][S:8][C:4]=2[N:5]=[CH:6][N:7]=1.[CH:12]([C:15]1[CH:20]=[CH:19][C:18]([CH:21]([NH2:23])[CH3:22])=[CH:17][CH:16]=1)([CH3:14])[CH3:13].C(N(CC)CC)C>CN(C=O)C.O>[Cl:11][C:10]1[C:3]2[C:2]([NH:23][CH:21]([C:18]3[CH:19]=[CH:20][C:15]([CH:12]([CH3:14])[CH3:13])=[CH:16][CH:17]=3)[CH3:22])=[N:7][CH:6]=[N:5][C:4]=2[S:8][CH:9]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 37280391-(4-Isopropylphenyl)ethanamine2×HCID 157457684,5-Dichlorothieno[2,3-d]pyrimidine

Product 1

HCID 58629060(5-Chlorothieno[2,3-d]pyrimidin-4-yl)-[1-(4-isopropylphenyl)ethyl]amineYield 87.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 4,5-dichlorothieno[2,3-d]pyrimidine (prepared as taught in EP 447,891) (775 mg, 3.8 mmol), 1-(4-isopropylphenyl)ethanamine (compound 95) (734 mg, 4.5 mmol), and triethylamine (767 mg, 7.6 mmol) in DMF (20 mL) was allowed to react for 24 hours at 20° C. The reaction mixture was diluted with water and extracted thrice with 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 (15 percent Et2O in pentane), yielding 1.1 g of oil.

Workup

  1. customto react for 24 hours at 20° C
  2. extractionextracted thrice with 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 (15 percent Et2O in pentane)

Sources & evidence

ORD record
ord-0eaed487a385406cba3fe6eaed1b590d
Source dataset
uspto-grants-2011_08
Patent number
US08008487B2

Linked notes

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