Methanol → HCID 15027677, compound

HRID 1090654Notes

Reaction equation

HRID 1090654 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][CH:17]=[CH: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][CH:18]=[CH: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 15027669HCID 15027669, compound

Product 1

HCID 15027677HCID 15027677, compoundYield 18%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Boron trifluoride (0.7 ml) was added to a solution of 7-benzyl-9-phenyl-4H,6H-pyrimido[6,1-b][1,3]thiazine-6,8(7H)-dione (1 g) in toluene (25 ml) and the mixture was refluxed for 15 hours. Methanol (7.5 ml) was added to the reaction solution at room temperature and the solution was stirred for 30 minutes. The reaction solution was concentrated to dryness, and acetone was added to the resulting residue to obtain the presipitate by filtration. The resulting crude crystals were washed and recrystallized from DMF-water to give yellow needles (0.13 g, 18%).

Workup

  1. temperaturethe mixture was refluxed for 15 hours
  2. concentrationThe reaction solution was concentrated to dryness, and acetone
  3. additionwas added to the resulting residue
  4. customto obtain the presipitate
  5. filtrationby filtration
  6. washThe resulting crude crystals were washed
  7. customrecrystallized from DMF-water

Sources & evidence

ORD record
ord-a8e3635f999f4ab78a44d4e6dc9b0d76
Source dataset
uspto-grants-1992_01
Patent number
US05082838

Reaction notes

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