HCID 21998635、化合物 → HCID 21998625、化合物

HRID 1976559ノート

反応式

HRID 1976559 の反応式
[NH2:1][C:2]1[N:7]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[C:11]([O:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH:10]=2)[C:6](=[S:25])[NH:5][C:4](=[O:26])[C:3]=1[NH:27][C:28](=O)[C:29]([O:32][CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)([CH3:31])[CH3:30].CC([O-])(C)C.[K+]>C(O)(C)C.ClCCl>[CH2:18]([O:17][C:11]1[CH:10]=[C:9]([CH:14]=[CH:13][C:12]=1[O:15][CH3:16])[CH2:8][N:7]1[C:2]2[N:1]=[C:28]([C:29]([O:32][CH2:33][C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)([CH3:30])[CH3:31])[NH:27][C:3]=2[C:4](=[O:26])[NH:5][C:6]1=[S:25])[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

参加物

5

反応物 2

HCID 21998635HCID 21998635、化合物HCID 23665647Potassium tert-butoxide

生成物 1

HCID 21998625HCID 21998625、化合物収率 69.9%

試薬・触媒・溶媒 2

HCID 3776Isopropanol溶媒HCID 6344Dichloromethane溶媒

実験手順

6-Amino-1-(3 -benzyloxy-4-methoxy-benzyl)-5-(2-benzyloxy-2-methyl-propionylamino)-2-thiouracil (46.54 g, 83 mmole) and 97% t-BuOK (38.41 g, 332 mmole) were heated under reflux in isopropanol (460 ml) for 50 minutes. The solvent was removed in vacuo, the residue dissolved in water (300 ml), treated twice with 5 g of charcoal, filtered, water added to a total volume of 500 ml and pH adjusted to neutral with a mixture of 5M HCl (60 ml) and sodium bicarbonate solution. The solid was collected at 10° C. to give 41.62 g of crude product, which was dissolved in dichloromethane (60 ml) and chromatographed over silicagel (126 g) using dichloromethane as eluant. Crystallization from methanol gave 3-(3-benzyloxy-4-methoxy-benzyl)-8-(1-benzyloxy-1-methyl-ethyl)-2-thioxanthine, (31.5 g, 69.9%) mp 290-302° C. (dec).

後処理

  1. customThe solvent was removed in vacuo
  2. dissolutionthe residue dissolved in water (300 ml)
  3. additiontreated twice with 5 g of charcoal
  4. filtrationfiltered
  5. additionwater added to a total volume of 500 ml
  6. additionneutral with a mixture of 5M HCl (60 ml) and sodium bicarbonate solution
  7. customThe solid was collected at 10° C.
  8. customto give 41.62 g of crude product, which
  9. customchromatographed over silicagel (126 g)
  10. customCrystallization from methanol

出典と根拠

ORDレコード
ord-7e555f6182354e258ca654dc15cd4025
出典データセット
uspto-grants-2001_05
特許番号
US06228859B1

反応ノート

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