Phosphorus pentachloride → 8-(4-Benzyloxy-phenyl)-2-chloro-1-propyl-1,7-dihydro-purin-6-one

HRID 925536노트

반응식

HRID 925536 반응식
[NH2:1][C:2]1[NH:7][C:6](=O)[N:5]([CH2:9][CH2:10][CH3:11])[C:4](=[O:12])[C:3]=1[NH:13][C:14](=O)[C:15]1[CH:20]=[CH:19][C:18]([O:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[CH:17][CH:16]=1.P(Cl)(Cl)(Cl)(Cl)[Cl:31]>P(Cl)(Cl)(Cl)=O>[CH2:22]([O:21][C:18]1[CH:19]=[CH:20][C:15]([C:14]2[NH:13][C:3]3[C:4](=[O:12])[N:5]([CH2:9][CH2:10][CH3:11])[C:6]([Cl:31])=[N:7][C:2]=3[N:1]=2)=[CH:16][CH:17]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

참가 물질

4

반응물 2

HCID 24819Phosphorus pentachlorideHCID 67133662N-(6-Amino-2,4-dioxo-3-propyl-1,2,3,4-tetrahydro-pyrimidin-5-yl)-4-benzyloxy-benzamide

생성물 1

HCID 674964518-(4-Benzyloxy-phenyl)-2-chloro-1-propyl-1,7-dihydro-purin-6-one수율 30.2%

시약·촉매·용매 1

HCID 24813Phosphorus oxychloride용매

실험 절차

The above N-(6-amino-2,4-dioxo-3-propyl-1,2,3,4-tetrahydro-pyrimidin-5-yl)-4-benzyloxy-benzamide (1.0 g, 0.0025 mol) and phosphorous pentachloride (0.64 g, 0.0025 mol) were taken in phosphorous oxy chloride (25 ml) and refluxed for 20 hours The mixture was cooled and solvent was removed. The residue was dissolved in water (20 ml) and extracted with DCM. (3×5 ml). The organic layer was washed with sat. NaHCO3 (30 ml) followed by saturated brine solution (2×30 ml) and dried over Na2SO4. Solvent was removed and the residue was further purified by column chromatography to obtain pure 8-(4-benzyloxy-phenyl)-2-chloro-1-propyl-1,7-dihydro-purin-6-one (0.298 g, 30%) as a yellow solid.

후처리

  1. temperaturerefluxed for 20 hours The mixture
  2. temperaturewas cooled
  3. customsolvent was removed
  4. dissolutionThe residue was dissolved in water (20 ml)
  5. extractionextracted with DCM
  6. washThe organic layer was washed with sat. NaHCO3 (30 ml)
  7. dry with materialdried over Na2SO4
  8. customSolvent was removed
  9. customthe residue was further purified by column chromatography

출처 및 근거

ORD 기록
ord-e5cf231a0ca448ba893247f5d4b34d54
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09284316B2

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