Ethyl Acetate → HCID 71237203, compound

HRID 2280800Notes

Reaction equation

HRID 2280800 reaction equation
[CH3:1][C:2]1([NH:5][C:6]2[N:11]=[C:10]([S:12][CH3:13])[C:9]([C:14]([NH2:16])=[O:15])=[CH:8][N:7]=2)[CH2:4][CH2:3]1.C1(C2[O:25]N2S(C2C=CC=CC=2)(=O)=O)C=CC=CC=1.C(OCC)(=O)C>C(Cl)(Cl)Cl>[CH3:1][C:2]1([NH:5][C:6]2[N:11]=[C:10]([S:12]([CH3:13])=[O:25])[C:9]([C:14]([NH2:16])=[O:15])=[CH:8][N:7]=2)[CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 3204052-(Benzenesulfonyl)-3-phenyloxaziridineHCID 712371065-Pyrimidinecarboxamide, 2-[(1-methylcyclopropyl)amino]-4-(methylthio)-

Product 1

HCID 71237203HCID 71237203, compoundYield 74.4%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a stirring solution of 2-(1-methylcyclopropylamino)-4-(methylthio)-pyrimidine-5-carboxamide (305 mg, 1.280 mmol) in chloroform (25.6 mL) was added portionwise 3-phenyl-2-(phenylsulfonyl)-1,2-oxaziridine (502 mg, 1.920 mmol). The resulting pale yellow solution was stirred at ambient temperature overnight. The reaction solution was concentrated under reduced pressure to give crude product as a white solid. Ethyl acetate (10 mL) was added and the slurry was stirred at room temperature for 1 h, filtered, washed with ethyl acetate, and dried in a vacuum oven for a few hours to afford 2-(1-methylcyclopropylamino)-4-(methylsulfinyl)pyrimidine-5-carboxamide (242 mg, 0.952 mmol, 74.4% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 8.35-8.90 (m, 2H), 7.88-8.14 (m, 1H), 7.28-7.59 (m, 1H), 2.74 (s, 3H), 1.32-1.46 (m, 3H), 0.68-0.84 (m, 2H), 0.50-0.70 (m, 2H). MS (ESI) m/z 255.0 [M+1]+.

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. customto give crude product as a white solid
  3. stirringthe slurry was stirred at room temperature 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-bb93b3dfae9f4d52b739cc99213824a8
Source dataset
uspto-grants-2015_09
Patent number
US09139534B2

Reaction notes

Loading…