Hydrochloric Acid → 1-[3,3-bis(methyloxy)propyl]-5-(4-isothiazolyl)-2,4(1H,3H)-pyrimidinedione

HRID 1925027노트

반응식

HRID 1925027 반응식
Cl.[S:2]1[CH:6]=[C:5]([C:7]2[C:8](=[O:14])[NH:9][C:10](=[O:13])[NH:11][CH:12]=2)[CH:4]=[N:3]1.C([O-])([O-])=O.[K+].[K+].Br[CH2:22][CH2:23][CH:24]([O:27][CH3:28])[O:25][CH3:26].Cl>CN(C)C=O.O>[CH3:26][O:25][CH:24]([O:27][CH3:28])[CH2:23][CH2:22][N:11]1[CH:12]=[C:7]([C:5]2[CH:4]=[N:3][S:2][CH:6]=2)[C:8](=[O:14])[NH:9][C:10]1=[O:13]

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 1189323-Bromopropionaldehyde dimethylacetalHCID 67519670HCID 67519670, 화합물

생성물 1

HCID 594483771-[3,3-bis(methyloxy)propyl]-5-(4-isothiazolyl)-2,4(1H,3H)-pyrimidinedione수율 13.44%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

5-(4-isothiazolyl)-2,4(1H,3H)-pyrimidinedione hydrochloride (Prep23, 300 mg, 1.036 mmol) was dissolved in N,N-Dimethylformamide (DMF) (4 ml) to give a pale yellow suspension. K2CO3 (215 mg, 1.554 mmol) was added ant the reaction mixture was stirred at room temperature for 1 h. 3-bromo-1,1-bis(methyloxy)propane (0.173 ml, 1.140 mmol) was added. Mixture was stirred at room temperature for 3 days, then diluted with water, acidified with diluted HCl until pH ˜5, and extracted with EtOAc. The organic phase was washed with water (3 times), brine, dried over Na2SO4, filtered and the solvent evaporated. The obtained residue was purified by flash chromatography eluting with cyclohexane/EtOAc 1:1. Obtained 60 mg (13.44% yield) of a 9:1 mixture of the title compound and the corresponding bis alkylated derivative.

후처리

  1. customto give a pale yellow suspension
  2. stirringMixture was stirred at room temperature for 3 days
  3. extractionextracted with EtOAc
  4. washThe organic phase was washed with water (3 times), brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customthe solvent evaporated
  8. customThe obtained residue was purified by flash chromatography
  9. washeluting with cyclohexane/EtOAc 1:1
  10. customObtained

출처 및 근거

ORD 기록
ord-e6711f020bb345af8d423ef606e16fde
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08178549B2

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