Triethylamine → HCID 58629120, compound

HRID 1678050Notes

Reaction equation

HRID 1678050 reaction equation
[CH3:1][O:2][C:3]([C:5]1[S:14][C:8]2[N:9]=[CH:10][N:11]=[C:12](Cl)[C:7]=2[C:6]=1[O:15][CH3:16])=[O:4].[CH3:17][O:18][C:19]1[CH:24]=[CH:23][C:22]([CH:25]([NH2:27])[CH3:26])=[CH:21][CH:20]=1.[CH2:28](N(CC)CC)C>CN(C=O)C.O>[CH2:1]([O:2][C:3]([C:5]1[S:14][C:8]2[N:9]=[CH:10][N:11]=[C:12]([NH:27][CH:25]([C:22]3[CH:23]=[CH:24][C:19]([O:18][CH3:17])=[CH:20][CH:21]=3)[CH3:26])[C:7]=2[C:6]=1[O:15][CH3:16])=[O:4])[CH3:28]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 2381811-(4-Methoxyphenyl)ethanamineHCID 86604625HCID 86604625, compound

Product 1

HCID 58629120HCID 58629120, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A stirred solution of 4-chloro-5-methoxythieno[2,3-d]pyrimidine-6-carboxylic acid methyl ester (1.0 g, 3.8 mmol), 1-(4-methoxyphenyl)ethylamine (0.8 g, 5 mmol) and triethylamine (1 mL) in DMF (20 mL) was warmed to 60° C. for 1 hour. The reaction was diluted with water (50 mL) and extracted with ethyl acetate (2×50 mL). The combined organic phases were washed with brine, dried (Na2SO4), filtered and concentrated. The crude product was purified by chromatography over silica gel (25 percent EtOAc in hexanes) affording product as a powder (700 mg, 1.5 mmol).

Workup

  1. extractionextracted with ethyl acetate (2×50 mL)
  2. washThe combined organic phases were washed with brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product was purified by chromatography over silica gel (25 percent EtOAc in hexanes)

Sources & evidence

ORD record
ord-cf4be60fd38542a488c33ea056140409
Source dataset
uspto-grants-2011_08
Patent number
US08008487B2

Reaction notes

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