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Triethylamine → HCID 18725654, 화합물

HRID 411852
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HRID 411852 반응식
[NH2:1][C@@H:2]1[CH2:6][CH2:5][N:4]([C:7]2[CH:12]=[CH:11][C:10]([C:13]([F:16])([F:15])[F:14])=[CH:9][N:8]=2)[CH2:3]1.[CH:17]1[N:22]=[C:21](Cl)[C:20]2[N:24]=[CH:25][N:26]([C@@H:27]3[O:31][C@H:30]([CH2:32][OH:33])[C@@H:29]([OH:34])[C@H:28]3[OH:35])[C:19]=2[N:18]=1.C(N(CC)CC)C.C(=O)(O)[O-].[Na+]>C(O)(C)C.C(Cl)Cl.C(O)C>[OH:33][CH2:32][C@@H:30]1[C@@H:29]([OH:34])[C@@H:28]([OH:35])[C@H:27]([N:26]2[CH:25]=[N:24][C:20]3[C:19]2=[N:18][CH:17]=[N:22][C:21]=3[NH:1][C@@H:2]2[CH2:6][CH2:5][N:4]([C:7]3[CH:12]=[CH:11][C:10]([C:13]([F:16])([F:15])[F:14])=[CH:9][N:8]=3)[CH2:3]2)[O:31]1
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참가 물질

8

반응물 4

HCID 8471TriethylamineHCID 930036-Chloropurine ribosideHCID 516892Sodium BicarbonateHCID 11401990HCID 11401990, 화합물

생성물 1

HCID 18725654HCID 18725654, 화합물

시약·촉매·용매 3

HCID 702Ethanol용매
HCID 3776
Isopropanol
용매
HCID 6344Dichloromethane용매

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온도
100 °C

실험 절차

267 mg 2-[(3R)-3-aminopyrrolidin-1-yl]-5-trifluoromethylpyridine, 331 mg 6-chloropurineriboside, 233 mg triethylamine, and 0.5 mL ethanol are combined and heated in a sealed vessel at 100° C. for about 5 hours. The mixture is cooled, partioned between methylene chloride (with some isopropyl alcohol added) and sodium bicarbonate. The organic layer is washed with brine, dried over magnesium sulfate, evaporated, and the residue purified by flash chromatography, eluting with 5% methanol in methylene chloride, to give (2R,3S,4R,5R)-2-hydroxymethyl-5-[6-[1-(5-trifluoromethylpyridin-2-yl)-pyrrolidin-3(R)-ylamino]purin-9-yl]tetrahydrofuran-3,4-diol, as the hemihydrate, m.p. 166-170° C.

후처리

  1. temperatureThe mixture is cooled
  2. washThe organic layer is washed with brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated
  5. customthe residue purified by flash chromatography
  6. washeluting with 5% methanol in methylene chloride

출처 및 근거

ORD 기록
ord-f6c90f79a210403aa530795ef9fb456f
출처 데이터셋
uspto-grants-2003_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06559313B2

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