HCID 21998635, compound → HCID 21998625, compound

HRID 1976559Notes

Reaction equation

HRID 1976559 reaction equation
[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

Participants

5

Reactant 2

HCID 21998635HCID 21998635, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 21998625HCID 21998625, compoundYield 69.9%

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 6344DichloromethaneSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-7e555f6182354e258ca654dc15cd4025
Source dataset
uspto-grants-2001_05
Patent number
US06228859B1

Reaction notes

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