Potassium Carbonate → 1-[3,3-bis(methyloxy)propyl]-5-(2,4-dimethyl-1,3-thiazol-5-yl)-2,4(1H,3H)-pyrimidinedione

HRID 1925036노트

반응식

HRID 1925036 반응식
[CH3:1][C:2]1[S:3][C:4]([C:8]2[C:9](=[O:15])[NH:10][C:11](=[O:14])[NH:12][CH:13]=2)=[C:5]([CH3:7])[N:6]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:23][CH2:24][CH:25]([O:28][CH3:29])[O:26][CH3:27]>CN(C)C=O>[CH3:27][O:26][CH:25]([O:28][CH3:29])[CH2:24][CH2:23][N:12]1[CH:13]=[C:8]([C:4]2[S:3][C:2]([CH3:1])=[N:6][C:5]=2[CH3:7])[C:9](=[O:15])[NH:10][C:11]1=[O:14]

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 1189323-Bromopropionaldehyde dimethylacetalHCID 594483615-(2,4-dimethyl-1,3-thiazol-5-yl)-2,4(1H,3H)-pyrimidinedione

생성물 1

HCID 594483571-[3,3-bis(methyloxy)propyl]-5-(2,4-dimethyl-1,3-thiazol-5-yl)-2,4(1H,3H)-pyrimidinedione수율 38.3%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a suspension of 5-(2,4-dimethyl-1,3-thiazol-5-yl)-2,4(1H,3H)-pyrimidinedione (Prep34, 250 mg, 1.120 mmol) in N,N-Dimethylformamide (DMF) (4 mL), Potassium carbonate (124 mg, 0.896 mmol) was added and the mixture was stirred at rt for 1 hour. Afterwards 3-bromo-1,1-bis(methyloxy)propane (0.170 mL, 1.120 mmol) was added dropwise and the reaction mixture was stirred at rt overnight. The day after the reaction was quenched with water and extracted with AcOEt. Organic phase was dried over Na2SO4 and concentrated under vacuum providing a crude as a clear oil. The latter was purified by flash chromatography (eluent:DCM/MeOH/NH3 97:3:0.1) affording the title compound (155 mg, 0.429 mmol) as a white solid.

후처리

  1. additionwas added
  2. stirringthe reaction mixture was stirred at rt overnight
  3. customThe day after the reaction was quenched with water
  4. extractionextracted with AcOEt
  5. dry with materialOrganic phase was dried over Na2SO4
  6. concentrationconcentrated under vacuum
  7. customproviding a crude as a clear oil
  8. customThe latter was purified by flash chromatography (eluent:DCM/MeOH/NH3 97:3:0.1)

출처 및 근거

ORD 기록
ord-8a3f806c88c54cb9b5ca9adc3fa41574
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08178549B2

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