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

HRID 1925024
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HRID 1925024 반응식
Cl.[CH3:2][C:3]1[S:4][CH:5]=[C:6]([C:8]2[C:9](=[O:15])[NH:10][C:11](=[O:14])[NH:12][CH:13]=2)[N:7]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:23][CH2:24][CH:25]([O:28][CH3:29])[O:26][CH3:27].Cl>CN(C)C=O.O>[CH3:27][O:26][CH:25]([O:28][CH3:29])[CH2:24][CH2:23][N:12]1[CH:13]=[C:8]([C:6]2[N:7]=[C:3]([CH3:2])[S:4][CH:5]=2)[C:9](=[O:15])[NH:10][C:11]1=[O:14]
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참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 1189323-Bromopropionaldehyde dimethylacetalHCID 675196935-(2-methyl-1,3-thiazol-4-yl)-2,4(1H,3H)-pyrimidinedione hydrochloride

생성물 1

HCID 594483461-[3,3-bis(methyloxy)propyl]-5-(2-methyl-1,3-thiazol-4-yl)-2,4(1H,3H)-pyrimidinedione수율 16.9%

시약·촉매·용매 2

HCID 962Water용매
HCID 6228Dimethylformamide용매

실험 절차

5-(2-methyl-1,3-thiazol-4-yl)-2,4(1H,3H)-pyrimidinedione hydrochloride (Prep20, 287 mg, 1.110 mmol) was dissolved in N,N-Dimethylformamide (DMF) (4 ml). K2CO3(460 mg, 3.33 mmol) were added and the reaction mixture stirred at room temperature for 1 h. 3-bromo-1,1-bis(methyloxy)propane (0.185 ml, 1.221 mmol) was added. The obtained mixture was then stirred at room temperature. After 4 days it was diluted with water, neutralized with HCl, and extracted by EtOAc. The organic phase was washed with water (3 times), brine, dried over Na2SO4, filtered and the solvent evaporated. The obtained crude was purified by preparative LC-MS. 58.5 mg of the title compound were isolated as a white solid.

후처리

  1. stirringThe obtained mixture was then stirred at room temperature
  2. extractionextracted by EtOAc
  3. washThe organic phase was washed with water (3 times), brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customthe solvent evaporated
  7. customThe obtained crude
  8. customwas purified by preparative LC-MS

출처 및 근거

ORD 기록
ord-c9aa1040da954c10aa125963e6c702bb
출처 데이터셋
uspto-grants-2012_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08178549B2

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