Ethyl Acetate → 2-(Bicyclo[1.1.1]pentan-1-ylamino)-4-(methylsulfinyl)pyrimidine-5-carboxamide

HRID 2280840Notes

Reaction equation

HRID 2280840 reaction equation
[C:1]12([NH:6][C:7]3[N:12]=[C:11]([S:13][CH3:14])[C:10]([C:15]([NH2:17])=[O:16])=[CH:9][N:8]=3)[CH2:5][CH:3]([CH2:4]1)[CH2:2]2.C1(C2[O:26]N2S(C2C=CC=CC=2)(=O)=O)C=CC=CC=1.C(OCC)(=O)C>C(Cl)(Cl)Cl>[C:1]12([NH:6][C:7]3[N:12]=[C:11]([S:13]([CH3:14])=[O:26])[C:10]([C:15]([NH2:17])=[O:16])=[CH:9][N:8]=3)[CH2:2][CH:3]([CH2:4]1)[CH2:5]2

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 3204052-(Benzenesulfonyl)-3-phenyloxaziridineHCID 709813662-(Bicyclo[1.1.1]pentan-1-ylamino)-4-(methylthio)pyrimidine-5-carboxamide

Product 1

HCID 709811922-(Bicyclo[1.1.1]pentan-1-ylamino)-4-(methylsulfinyl)pyrimidine-5-carboxamideYield 91%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a stirring solution of 2-(bicyclo[1.1.1]pentan-1-ylamino)-4-(methylthio)pyrimidine-5-carboxamide (410 mg, 1.638 mmol) in chloroform (39.0 mL) was added portionwise, 3-phenyl-2-(phenylsulfonyl)-1,2-oxaziridine (514 mg, 1.965 mmol). The resulting pale yellow solution was stirred at ambient temperature for two nights under nitrogen. The reaction mixture was concentrated under reduced pressure to give the crude product as a white solid. Ethyl acetate (15 mL) was added to these solids and the slurry was stirred at room temp for 1 h, filtered, washed with ethyl acetate, and dried in a vacuum oven for a few hours to afford 2-(bicyclo[1.1.1]pentan-1-ylamino)-4-(methylsulfinyl)pyrimidine-5-carboxamide (397 mg, 1.491 mmol, 91% yield) as white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.67-9.14 (m, 2H), 7.93-8.11 (m, 1H), 7.41-7.54 (m, 1H), 2.68-2.79 (m, 3H), 2.43-2.48 (m, 1H), 2.02-2.21 (m, 6H). MS (ESI) m/z 267.0 [M+1]+.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customto give the crude product as a white solid
  3. stirringthe slurry was stirred at room temp for 1 h
  4. filtrationfiltered
  5. washwashed with ethyl acetate
  6. customdried in a vacuum oven for a few hours

Sources & evidence

ORD record
ord-01720893dcf64f5c8a6868e5605075f6
Source dataset
uspto-grants-2015_09
Patent number
US09139534B2

Reaction notes

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