Ethyl Acetate → 7-(1-aminoethyl)-6-(3-fluorophenyl)-5H-[1,3]thiazolo[3,2-a]pyrimidin-5-one

HRID 58274Notes

Reaction equation

HRID 58274 reaction equation
[N:1]([CH:4]([C:6]1[N:7]=[C:8]2[S:22][CH:21]=[CH:20][N:9]2[C:10](=[O:19])[C:11]=1[C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[CH:13]=1)[CH3:5])=[N+]=[N-].CP(C)C.C(OCC)(=O)C>O1CCCC1.O>[NH2:1][CH:4]([C:6]1[N:7]=[C:8]2[S:22][CH:21]=[CH:20][N:9]2[C:10](=[O:19])[C:11]=1[C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[CH:13]=1)[CH3:5]

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 68983TrimethylphosphineHCID 866500737-(1-azidoethyl)-6-(3-fluorophenyl)-5H-[1,3]thiazolo[3,2-a]pyrimidin-5-one

Product 1

HCID 581113987-(1-aminoethyl)-6-(3-fluorophenyl)-5H-[1,3]thiazolo[3,2-a]pyrimidin-5-oneYield 58.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of 7-(1-azidoethyl)-6-(3-fluorophenyl)-5H-[1,3]thiazolo[3,2-a]pyrimidin-5-one (0.32 g, 1.0 mmol) in tetrahydrofuran (5 mL) and water (1 mL) was added 1.00 M of trimethylphosphine in tetrahydrofuran (1.22 mL, 1.22 mmol) at room temperature, and the mixture was stirred at room temperature for 1 hour. To the mixture was added ethyl acetate, and the mixture was extracted with aqueous 1 N HCl solution (three times). The combined extract was neutralized with solid NaHCO3 and extracted with dichloromethane (two times). The combined organic layer was washed with brine, dried over Na2SO4, and concentrated to give the desired product (0.17 g, 58%). LCMS calculated for C14H13FN3OS (M+H)+: m/z=290.1. Found: 290.0.

Workup

  1. extractionthe mixture was extracted with aqueous 1 N HCl solution (three times)
  2. extractionThe combined extract
  3. extractionextracted with dichloromethane (two times)
  4. washThe combined organic layer was washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-05ae71beb8ca49c184a90b492f2ca426
Source dataset
uspto-grants-2016_09
Patent number
US09434746B2

Reaction notes

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