Triethylamine → HCID 69508536, compound

HRID 1179136Notes

Reaction equation

HRID 1179136 reaction equation
CN(C)CCN[C:6]1[N:11]=[C:10]([O:12][C:13]2C3C(=CC=CC=3)C(NC(NC3C=C(C(F)(F)F)C=CC=3OC)=O)=CC=2)[CH:9]=[C:8](C)[N:7]=1.CO[C:43]1[CH:50]=[CH:49][C:46]([CH2:47][NH2:48])=[CH:45][CH:44]=1.C(N(CC)CC)C.C(OCC)(=O)C>CS(C)=O.O>[CH3:13][O:12][C:10]1[CH:9]=[CH:8][N:7]=[C:6]([NH:48][CH2:47][C:46]2[CH:45]=[CH:44][CH:43]=[CH:50][CH:49]=2)[N:11]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 754524-MethoxybenzylamineHCID 9807724HCID 9807724, compound

Product 1

HCID 69508536HCID 69508536, compoundYield 56.1%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

(4-Boc-amino-naphthyl)-(2-chloro-6-methyl-pyrimidinyl)-ether (see Example 1) (2.00 g, 5.18 mmol), 4-methoxybenzylamine (0.69 mL, 5.18 mmol) and triethylamine (0.73 mL, 5.18 mmol) were dissolved in 10 mL DMSO in a sealed tube. The tube was sealed and placed into a 95° C. oil bath. The reaction was stirred overnight, then cooled and ethyl acetate and water were added. The aqueous layer was washed twice with EtOAc. The organic extracts were combined, washed once with brine, dried (Na2SO4), filtered and concentrated in vacuo. The residue was dissolved in dichloromethane and purified by column chromatography on silica gel eluting with EtOAc/hexane, providing 0.625 g of the desired 4-methoxybenzylamino-pyrimidine intermediate as a bright yellow solid.

Workup

  1. customThe tube was sealed
  2. customplaced into a 95° C.
  3. temperaturecooled
  4. washThe aqueous layer was washed twice with EtOAc
  5. washwashed once with brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. dissolutionThe residue was dissolved in dichloromethane
  10. custompurified by column chromatography on silica gel eluting with EtOAc/hexane

Sources & evidence

ORD record
ord-b53ccaf7170748b8b99eabcb10f8e2b1
Source dataset
uspto-grants-2007_10
Patent number
US07279475B2

Reaction notes

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