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

HRID 58270Notes

Reaction equation

HRID 58270 reaction equation
[N:1]([CH:4]([C:6]1[N:7]=[C:8]2[S:23][CH:22]=[CH:21][N:9]2[C:10](=[O:20])[C:11]=1[C:12]1[CH:17]=[C:16]([F:18])[CH:15]=[C:14]([F:19])[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:23][CH:22]=[CH:21][N:9]2[C:10](=[O:20])[C:11]=1[C:12]1[CH:17]=[C:16]([F:18])[CH:15]=[C:14]([F:19])[CH:13]=1)[CH3:5]

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 68983TrimethylphosphineHCID 866500727-(1-azidoethyl)-6-(3,5-difluorophenyl)-5H-[1,3]thiazolo[3,2-a]pyrimidin-5-one

Product 1

HCID 581114057-(1-aminoethyl)-6-(3,5-difluorophenyl)-5H-[1,3]thiazolo[3,2-a]pyrimidin-5-oneYield 88.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of 7-(1-azidoethyl)-6-(3,5-difluorophenyl)-5H-[1,3]thiazolo[3,2-a]pyrimidin-5-one (0.295 g, 0.885 mmol) in tetrahydrofuran (5 mL) and water (1 mL) was added 1.00 M of trimethylphosphine in tetrahydrofuran (1.06 mL, 1.06 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 layers were washed with brine, dried over Na2SO4, and concentrated to give the desired compound (0.241 g, 88.6%), which was used directly in next step. LCMS calculated for C14H12F2N3OS (M+H)+: m/z=308.1. Found: 308.0.

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 layers were washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-e68be30492f5462686160b0013648742
Source dataset
uspto-grants-2016_09
Patent number
US09434746B2

Reaction notes

Loading…