Bis(p-nitrophenyl) phosphate → 5-Amino-3-(2',3,5'-tri-O-acetyl-beta-D-ribofuranosyl)-3H-thiazolo[4,5-d]pyrimidin-2-one

HRID 2252411

반응식

HRID 2252411 반응식
[NH2:1][C:2]1[N:3]=[CH:4][C:5]2[S:10][C:9](=[O:11])[NH:8][C:6]=2[N:7]=1.C(O)(=O)C.C(O)(=O)C.C(O)(=O)C.C(O)(=O)C.C(O[C@@H:32]1[O:44][C@H:43]([CH2:45][O:46][C:47](=[O:49])[CH3:48])[C@@H:38]([O:39][C:40](=[O:42])[CH3:41])[C@H:33]1[O:34][C:35](=[O:37])[CH3:36])(=O)C.P(O)(OC1C=CC([N+]([O-])=O)=CC=1)(OC1C=CC([N+]([O-])=O)=CC=1)=O>>[NH2:1][C:2]1[N:3]=[CH:4][C:5]2[S:10][C:9](=[O:11])[N:8]([C@@H:32]3[O:44][C@H:43]([CH2:45][O:46][C:47](=[O:49])[CH3:48])[C@@H:38]([O:39][C:40](=[O:42])[CH3:41])[C@H:33]3[O:34][C:35](=[O:37])[CH3:36])[C:6]=2[N:7]=1

참가 물질

4

반응물 3

HCID 255Bis(p-nitrophenyl) phosphateHCID 247640395-Amino-3H-thiazolo[4,5]pyrimidine-2-oneHCID 671510951,2,3,5-tetra-O-acetyl-beta-D-ribofuranose tetraacetate

생성물 1

HCID 116332675-Amino-3-(2',3,5'-tri-O-acetyl-beta-D-ribofuranosyl)-3H-thiazolo[4,5-d]pyrimidin-2-one수율 40%

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온도
150 °C

실험 절차

Compound 86 (62 mg, 0.4 mmol), 1,2,3,5-tetra-O-acetyl-β-D-ribofuranose tetraacetate (128 mg, 0.4 mmol), and catalytic bis(p-nitrophenyl) hydrogen phosphate (13 mg, 0.04 mmol) were mixed and placed in a 500 ml flask. The reaction vessel was carefully placed under vacuum (˜5.0 mmHg) and lowered into an oil bath heated at 150° C. for 10 minutes. After cooling to room temperature, the solids were washed with ethyl acetate. The crude product was purified by flash column. (silica, 5 to 35% ethyl acetate gradient in chloroform) to yield 68 mg of compound 79 (40%) as a white solid as a white powder identical in all respects to material isolated in Example 38, step 2.

후처리

  1. customplaced in a 500 ml flask
  2. customlowered into an oil bath
  3. temperatureAfter cooling to room temperature
  4. washthe solids were washed with ethyl acetate
  5. customThe crude product was purified by flash column

출처 및 근거

ORD 기록
ord-25078ec8d8a04a4e80724fcad8da4013
출처 데이터셋
uspto-grants-2008_01
특허 번호
US07321033B2

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