N-Iodosuccinimide → (R)-Tert-butyl 3-(5-iodo-6-methoxy-2-morpholinopyrimidin-4-ylamino)piperidine-1-carboxylate

HRID 1507489Notes

Reaction equation

HRID 1507489 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[C:7]([N:9]2[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)[N:6]=[C:5]([NH:15][C@@H:16]2[CH2:21][CH2:20][CH2:19][N:18]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:17]2)[CH:4]=1.C1C(=O)N([I:36])C(=O)C1>C(#N)C>[I:36][C:4]1[C:5]([NH:15][C@@H:16]2[CH2:21][CH2:20][CH2:19][N:18]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:17]2)=[N:6][C:7]([N:9]2[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)=[N:8][C:3]=1[O:2][CH3:1]

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 117677757HCID 117677757, compound

Product 1

HCID 89554305(R)-Tert-butyl 3-(5-iodo-6-methoxy-2-morpholinopyrimidin-4-ylamino)piperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Compound 20 (113 mg, 0.287 mmol) was dissolved in acetonitrile (3 mL) and NIS (129 mg, 0.574 mmol) was added. The solution was heated to reflux for 1 h. The solvent was evaporated and the residue dissolved in EtOAc, washed with sat. NaHCO3, NaS2O3, water, and brine. The organics were dried (MgSO4), filtered and concentrated. The residue was purified by column chromatography on silica gel, eluting with EtOAc/hexane to give the title compound as a colorless foam. 1H NMR (CDCl3) δ 5.07 (d, J=6.8 Hz, 1H), 3.99 (br s, 1H), 3.88 (s, 3H), 3.86-3.73 (m, 8H), 3.43 (br s, 3H), 1.90-1.86 (m, 1H), 1.70-1.63 (m, 2H), 1.56-1.55 (m, 1H), 1.42 (s, 9H); LCMS 2.95 min, 520 (M+H).

Workup

  1. temperatureThe solution was heated
  2. temperatureto reflux for 1 h
  3. customThe solvent was evaporated
  4. dissolutionthe residue dissolved in EtOAc
  5. washwashed with sat. NaHCO3, NaS2O3, water, and brine
  6. dry with materialThe organics were dried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified by column chromatography on silica gel
  10. washeluting with EtOAc/hexane

Sources & evidence

ORD record
ord-437cd080a15e4428bb0b79bc53bf3a3a
Source dataset
uspto-grants-2015_12
Patent number
US09221809B2

Reaction notes

Loading…