Methanol → 6-[(4,5-Dichloro-2-methyl-1H-imidazol-1-yl)methyl]-1,2,3,4-tetrahydro-3-methyl-1-(isobutyl)-2,4-dioxothieno[2,3-d]pyrimidine-5-carboxylic acid

HRID 131556노트

반응식

HRID 131556 반응식
[OH-].[Na+].CO.[Cl:5][C:6]1[N:7]=[C:8]([CH3:33])[N:9]([CH2:12][C:13]2[S:28][C:16]3[N:17]([CH2:24][CH:25]([CH3:27])[CH3:26])[C:18](=[O:23])[N:19]([CH3:22])[C:20](=[O:21])[C:15]=3[C:14]=2[C:29]([O:31]C)=[O:30])[C:10]=1[Cl:11]>O1CCCC1>[Cl:5][C:6]1[N:7]=[C:8]([CH3:33])[N:9]([CH2:12][C:13]2[S:28][C:16]3[N:17]([CH2:24][CH:25]([CH3:27])[CH3:26])[C:18](=[O:23])[N:19]([CH3:22])[C:20](=[O:21])[C:15]=3[C:14]=2[C:29]([OH:31])=[O:30])[C:10]=1[Cl:11]

참가 물질

5

반응물 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 11453923Methyl 6-[4,5-dichloro-2-methyl-1H-imidazol-1-ylmethyl]-1,2,3,4-tetrahydro-3-methyl-1-(2-methylpropyl)-2,4-dioxo-thieno[2,3-d]pyrimidine-5-carboxylate

생성물 1

HCID 113628036-[(4,5-Dichloro-2-methyl-1H-imidazol-1-yl)methyl]-1,2,3,4-tetrahydro-3-methyl-1-(isobutyl)-2,4-dioxothieno[2,3-d]pyrimidine-5-carboxylic acid

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

Sodium hydroxide (7.3 ml of 1M aqueous solution) followed by methanol (4 ml) were added to a solution of the product of step c) (2.28 g) in tetrahydrofuran (50 ml) and stirred at room temperature for 3 h. The solution was concentrated under reduced pressure. The residue was diluted with water and extracted with ethyl acetate. The combined extracts were dried over magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by flash silica chromatography eluting with a gradient of 2-5% ethanol in dichloromethane to give the sub-title compound as a white solid (1.68 g). MS (APCI) 445/447 [M+H]+. δ 1HCDCl3 0.96 (6H,d), 2.22 (1H, septet), 2.37 (3H,s), 3.51 (3H,s), 3.78 (2H,d), 5.78 (2H,s), 15.51 (1H,br.s).

후처리

  1. concentrationThe solution was concentrated under reduced pressure
  2. additionThe residue was diluted with water
  3. extractionextracted with ethyl acetate
  4. dry with materialThe combined extracts were dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash silica chromatography
  8. washeluting with a gradient of 2-5% ethanol in dichloromethane

출처 및 근거

ORD 기록
ord-263ec2d36204410a833f7f2d11602e2e
출처 데이터셋
uspto-grants-2008_06
특허 번호
US07384950B2

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