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Water → 2-(4-Methoxy-3,5-dimethylphenyl)-5-methylsulfanyl-7-propoxyoxazolo[5,4-d]pyrimidine

HRID 403462
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HRID 403462 반응식
[CH3:1][O:2][C:3]1[C:8]([CH3:9])=[CH:7][C:6]([C:10]2[O:11][C:12]3[N:13]=[C:14]([S:20][CH3:21])[N:15]=[C:16]([OH:19])[C:17]=3[N:18]=2)=[CH:5][C:4]=1[CH3:22].C(=O)([O-])[O-].[K+].[K+].Br[CH2:30][CH2:31][CH3:32].O>CN(C)C=O>[CH3:1][O:2][C:3]1[C:4]([CH3:22])=[CH:5][C:6]([C:10]2[O:11][C:12]3[N:13]=[C:14]([S:20][CH3:21])[N:15]([CH2:30][CH2:31][CH3:32])[C:16](=[O:19])[C:17]=3[N:18]=2)=[CH:7][C:8]=1[CH3:9].[CH3:1][O:2][C:3]1[C:4]([CH3:22])=[CH:5][C:6]([C:10]2[O:11][C:12]3[N:13]=[C:14]([S:20][CH3:21])[N:15]=[C:16]([O:19][CH2:30][CH2:31][CH3:32])[C:17]=3[N:18]=2)=[CH:7][C:8]=1[CH3:9]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 962WaterHCID 78401-BromopropaneHCID 11430Potassium CarbonateHCID 178489873HCID 178489873, 화합물

생성물 2

HCID 672941732-(4-Methoxy-3,5-dimethylphenyl)-5-methylsulfanyl-7-propoxyoxazolo[5,4-d]pyrimidineHCID 67294209HCID 67294209, 화합물

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
60 °C

실험 절차

5.9 g of 2-(4-methoxy-3,5-dimethyl-phenyl)-5-methylsulfanyl-oxazolo[5,4-d]pyrimidin-7-ol were dissolved in 150 ml of N,N-dimethylformamide, and 7.7 g of potassium carbonate and then 2.7 g of 1-bromo-propane were added. The solution was stirred at 60° C. for 5 h and then, after cooling, poured onto 150 ml of water. The precipitate was filtered off with suction. The obtained mixture of regioisomers was purified by silica gel chromatography (50 g silica (solute cartridge, heptane/ethyl acetate 9/1). Besides 1.4 g of 2-(4-methoxy-3,5-dimethyl-phenyl)-5-methylsulfanyl-6-propyl-6H-oxazolo[5,4-d]pyrimidin-7-one (LC/MS (method LC1): Rt=1.43 min; m/z=360.13 [M+H]+), 2.5 g of the title compound were obtained.

후처리

  1. temperatureafter cooling
  2. filtrationThe precipitate was filtered off with suction
  3. additionThe obtained mixture of regioisomers
  4. customwas purified by silica gel chromatography (50 g silica (solute cartridge, heptane/ethyl acetate 9/1)

출처 및 근거

ORD 기록
ord-0994a361c85c4b329b52a1a3e56c1541
출처 데이터셋
uspto-grants-2014_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08748436B2

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