Ethyl 2-(methylsulfonyl)pyrimidine-5-carboxylate → HCID 58417050, compound

HRID 1805283Notes

Reaction equation

HRID 1805283 reaction equation
CS([C:5]1[N:10]=[CH:9][C:8]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:7][N:6]=1)(=O)=O.[NH2:16][C@H:17]1[CH2:21][CH2:20][NH:19][CH2:18]1>COCCOC>[NH2:16][C@H:17]1[CH2:21][CH2:20][N:19]([C:5]2[N:10]=[CH:9][C:8]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:7][N:6]=2)[CH2:18]1

Participants

4

Reactant 2

HCID 254889Ethyl 2-(methylsulfonyl)pyrimidine-5-carboxylateHCID 1519351(3S)-(-)-3-Aminopyrrolidine

Product 1

HCID 58417050HCID 58417050, compoundYield 90.3%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

The methylsulfone 149 (450 mg, 1.95 mmol) was added to a solution of 3-(S)(−) aminopyrrolidine (253 mg, 2.93 mmol) in DME (10 ml). The reaction mixture was stirred for 10 min at room temperature and the solvent was evaporated. The remaining solid was dissolved in dichloromethane, the solution was washed with saturated aqueous NaHCO3 and brine, dried over MgSO4, filtered and concentrated in vacuo to afford the title compound 150 as a yellow solid (416 mg, 90% yield). 1H NMR: (DMSO) δ (ppm): 8.76 (s, 2H), 4.26 (q, J=7.1 Hz, 2H), 3.70-3.53 (m, 4H), 3.26 (dd, J=11.3, 3.9 Hz, 1H), 2.07-1.98 (m, 1H), 1.75-1.67 (m, 3H), 1.29 (t, J=7.0 Hz, 3H). LRMS (ESI): (calc.) 236.1; (obt.) 237.2 (M+H)+.

Workup

  1. customthe solvent was evaporated
  2. dissolutionThe remaining solid was dissolved in dichloromethane
  3. washthe solution was washed with saturated aqueous NaHCO3 and brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-872a6ba826214f039239aa19b897154b
Source dataset
uspto-grants-2013_01
Patent number
US08354445B2

Reaction notes

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