Sodium Methoxide → 2-Methyl-1-(-beta-D-ribofuranosyl)pyrimidin-4-one

HRID 840612

반응식

HRID 840612 반응식
[CH3:1][C:2]1[N:3]([C@@H:9]2[O:31][C@H:30]([CH2:32][O:33]C(=O)C3C=CC=CC=3)[C@@H:20]([O:21]C(=O)C3C=CC=CC=3)[C@H:10]2[O:11]C(=O)C2C=CC=CC=2)[CH:4]=[CH:5][C:6](=[O:8])[N:7]=1.C[O-].[Na+]>CO>[CH3:1][C:2]1[N:3]([C@@H:9]2[O:31][C@H:30]([CH2:32][OH:33])[C@@H:20]([OH:21])[C@H:10]2[OH:11])[CH:4]=[CH:5][C:6](=[O:8])[N:7]=1

참가 물질

4

반응물 2

HCID 10942334Sodium MethoxideHCID 120421992-Methyl-1-(2',3'5'-tri-o-benzoyl-beta-d-ribofuranosyl)-pyrimidin-4-one

생성물 1

HCID 103994612-Methyl-1-(-beta-D-ribofuranosyl)pyrimidin-4-one수율 39.1%

시약·촉매·용매 1

HCID 887Methanol용매2회

실험 절차

To a solution of 2-methyl-1-(2′,3′5′-tri-O-benzoyl-β-D-ribofuranosyl)-pyrimidin-4-one (13.86 g, 25 mmol) in methanol (150 ml) was added 4.37 N sodium methoxide solution in MeOH (2.5 mmol, 0.1 eq.). The solution was stirred overnight at room temperature and then evaporated. The residue was partitioned between water (100 ml) and dichloromethane (2×150 ml). The aqueous layer was neutralized with Dowex 50H+-form and evaporated. The orange oily residue was crystallized from ethanol/acetone 3:1 to give the title compound (2.37 g, 39%). 1H-NMR (CDCl3): δ8.1 (d, 1H, H6); 6.0 (d, 1H, H5); 5.65 (m, 2H, H1′, 2′-OH); 5.25, 5.2 (d,t, 2H, 3′-OH, 5′-OH); 2.45 (s, 3H, CH3)

후처리

  1. customevaporated
  2. customThe residue was partitioned between water (100 ml) and dichloromethane (2×150 ml)
  3. customevaporated
  4. customThe orange oily residue was crystallized from ethanol/acetone 3:1

출처 및 근거

ORD 기록
ord-edcfc51c5e7f4bbeb2cc3d831f08d8a0
출처 데이터셋
uspto-grants-2002_04
특허 번호
US06369040B1

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