Methanol → HCID 15027610, compound

HRID 1090639Notes

Reaction equation

HRID 1090639 reaction equation
B(F)(F)F.C([N:12]1[C:21](=[O:22])[C:20]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[C:15]2[S:16][CH2:17][CH2:18][CH2:19][N:14]2[C:13]1=[O:29])C1C=CC=CC=1.CO>C1(C)C=CC=CC=1>[C:23]1([C:20]2[C:21](=[O:22])[NH:12][C:13](=[O:29])[N:14]3[CH2:19][CH2:18][CH2:17][S:16][C:15]=23)[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 6356Boron trifluorideHCID 15027578HCID 15027578, compound

Product 1

HCID 15027610HCID 15027610, compoundYield 44.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Boron trifluoride (0.68 ml) was added to a solution of 7-benzyl-9-phenyl-3,4-dihydro-2H,6H-pyrimido[6,1-b][1,3]thiazine-6,8(7H)-dione (1 g) in toluene (40 ml) and was refluxed for 14 hours. Methanol (7 ml) was added to the reaction solution and the mixture was stirred for 30 minutes. The resulting solution was concentrated to dryness, and the residue was dissolved in methylene chloride and ethyl ether. The insoluble material was obtained by filtration and the product was washed by aqueous methanol. After the washing, it was recrystallized from DMF-water to give colorless crystals (0.33 g, 44%).

Workup

  1. temperaturewas refluxed for 14 hours
  2. concentrationThe resulting solution was concentrated to dryness
  3. dissolutionthe residue was dissolved in methylene chloride
  4. customThe insoluble material was obtained by filtration
  5. washthe product was washed by aqueous methanol
  6. customAfter the washing, it was recrystallized from DMF-water

Sources & evidence

ORD record
ord-439310a9eb5f4580aa48c7a8df94e37d
Source dataset
uspto-grants-1992_01
Patent number
US05082838

Reaction notes

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