2-Aminopyrimidine → 2-oxo-N-(pyrimidin-2-yl)oxazolidine-3-sulfonamide

HRID 2172295Notes

Reaction equation

HRID 2172295 reaction equation
Cl[S:2]([N:5]=[C:6]=[O:7])(=[O:4])=[O:3].Br[CH2:9][CH2:10][OH:11].[N:12]1[CH:17]=[CH:16][CH:15]=[N:14][C:13]=1[NH2:18].C(N(CC)CC)C>C(Cl)Cl>[O:7]=[C:6]1[N:5]([S:2]([NH:18][C:13]2[N:14]=[CH:15][CH:16]=[CH:17][N:12]=2)(=[O:4])=[O:3])[CH2:9][CH2:10][O:11]1

Participants

6

Reactant 4

HCID 79782-AminopyrimidineHCID 8471TriethylamineHCID 108982-BromoethanolHCID 70918Chlorosulfonyl isocyanate

Product 1

HCID 898134912-oxo-N-(pyrimidin-2-yl)oxazolidine-3-sulfonamideYield 36.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

In a 200-mL round-bottom flask was charged with DCM (50 mL) and chlorosulfonyl isocyanate (0.913 ml, 10.51 mmol). The flask was cooled in an ice-bath for 20 min, then 2-bromoethanol (0.745 ml, 10.51 mmol) was added dropwise. The mixture was stirred for 2.5 h, then a solution of pyrimidin-2-amine (1.00 g, 10.51 mmol) and triethylamine (4.40 ml, 31.5 mmol) in DCM (30 mL) was added dropwise via an addition funnel over 10 min. When the addition was complete, the cooling bath was removed, and the mixture was stirred for 2 days. The mixture was washed with 2 N aq. HCl, and the aq. layer was extracted with DCM. The combined organic extracts were dried over sodium sulfate, filtered, and concentrated. The mixture was taken up in a mixture of DCM and EtOAc, then filtered and dried under a stream of nitrogen to give 2-oxo-N-(pyrimidin-2-yl)oxazolidine-3-sulfonamide (0.930 g, 3.81 mmol, 36.2) as a cream-colored solid. 1H NMR (400 MHz, DMSO-d6) δ ppm=12.98 (br. s, 1H), 8.66 (s, 2H), 7.13 (t, J=5.0 Hz, 1H), 4.44-4.18 (m, 4H).

Workup

  1. temperatureThe flask was cooled in an ice-bath for 20 min
  2. additionWhen the addition
  3. customthe cooling bath was removed
  4. stirringthe mixture was stirred for 2 days
  5. washThe mixture was washed with 2 N aq. HCl
  6. extractionthe aq. layer was extracted with DCM
  7. dry with materialThe combined organic extracts were dried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. additionThe mixture was taken up in a mixture of DCM and EtOAc
  11. filtrationfiltered
  12. customdried under a stream of nitrogen

Sources & evidence

ORD record
ord-65a1b79030fc4b289266f1f96d650cf4
Source dataset
uspto-grants-2015_06
Patent number
US09051311B2

Reaction notes

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