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Potassium Carbonate → HCID 90403261, 화합물

HRID 2200550
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HRID 2200550 반응식
[Br:1][C:2]1[NH:10][C:9]2[C:8](=[O:11])[N:7]([CH2:12][CH2:13][CH2:14][OH:15])[C:6](=[O:16])[N:5]([CH3:17])[C:4]=2[N:3]=1.Cl[CH2:19][C:20]1[S:21][C:22]([CH3:25])=[CH:23][N:24]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.CCCC[N+](CCCC)(CCCC)CCCC.[I-]>[Br:1][C:2]1[N:10]([CH2:19][C:20]2[S:21][C:22]([CH3:25])=[CH:23][N:24]=2)[C:9]2[C:8](=[O:11])[N:7]([CH2:12][CH2:13][CH2:14][OH:15])[C:6](=[O:16])[N:5]([CH3:17])[C:4]=2[N:3]=1
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참가 물질

6

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HCID 11430Potassium CarbonateHCID 205558492-(Chloromethyl)-5-methyl-1,3-thiazole hydrochloride2회HCID 90402404HCID 90402404, 화합물

생성물 1

HCID 90403261HCID 90403261, 화합물수율 58.5%

시약·촉매·용매 2

HCID 67553Tetrabutylammonium Iodide촉매
HCID 6228
Dimethylformamide
용매

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온도
60 °C

실험 절차

To a solution of 8-bromo-1-(3-hydroxypropyl)-3-methyl-1H-purine-2,6(3H,7H)-dione (0.5 g, 1.65 mmol) in DMF (50 mL) was added 2-(chloromethyl)-5-methylthiazole (0.27 g, 1.81 mmol, intermediate 4), potassium carbonate (0.34 g, 2.48 mmol) and TBAI (2 mg, 0.02 mmol). The mixture was heated at 60° C. for 3 h. The mixture was cooled; then partitioned between ethyl acetate and water. The organic layers were combined, dried over sodium sulfate, filtered and concentrated. The residue was purified by a column chromatography eluting with DCM/methanol (60:1 to 30:1) to give 8-bromo-1-(3-hydroxypropyl)-3-methyl-7-((5-methylthiazol-2-yl)methyl)-1H-purine-2,6(3H,7H)-dione (0.4 g, 58.4%) as a yellow oil which was used without further purification. LCMS MH+ 416.

후처리

  1. temperatureThe mixture was cooled
  2. customthen partitioned between ethyl acetate and water
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by a column chromatography
  7. washeluting with DCM/methanol (60:1 to 30:1)

출처 및 근거

ORD 기록
ord-11bfea2db7c4464693b16119c46874c4
출처 데이터셋
uspto-grants-2016_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09359359B2

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