Trifluoroacetic acid → (+/-)-5-[7-Ethyl-2-methyl-4H-benzo[5,6]cyclohepta[1,2-d]thiazol-4-yl]-1-methyl-2,4(1H,3H)-pyrimidinedione

HRID 324464

Reaction equation

HRID 324464 reaction equation
[CH3:1][N:2]1[CH:9]=[CH:8][C:6](=[O:7])[NH:5][C:3]1=[O:4].[CH2:10]([C:12]1[CH:13]=[CH:14][C:15]2[CH:25](O)[C:20]3[N:21]=[C:22]([CH3:24])[S:23][C:19]=3[CH:18]=[CH:17][C:16]=2[CH:27]=1)[CH3:11].FC(F)(F)C(O)=O>ClCCl>[CH2:10]([C:12]1[CH:13]=[CH:14][C:15]2[CH:25]([C:8]3[C:6](=[O:7])[NH:5][C:3](=[O:4])[N:2]([CH3:1])[CH:9]=3)[C:20]3[N:21]=[C:22]([CH3:24])[S:23][C:19]=3[CH:18]=[CH:17][C:16]=2[CH:27]=1)[CH3:11]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 120091-MethyluracilHCID 70113719(+/-)-7-Ethyl-2-methyl-4H-benzo[5,6]cyclohepta[1,2-d]thiazol-4-ol

Product 1

HCID 70113042(+/-)-5-[7-Ethyl-2-methyl-4H-benzo[5,6]cyclohepta[1,2-d]thiazol-4-yl]-1-methyl-2,4(1H,3H)-pyrimidinedione

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-Methyluracil (0.064 g) was added to a solution of the product from step (xi) (0.10 g) in dichloromethane (2 ml), followed by trifluoroacetic acid (1 ml). The orange solution was stirred at room temperature for 10 minutes before the solvent was removed under reduced pressure. The residue was azeotroped twice with acetonitrile, and the crude product purified by chromatography, eluting with 0-5% methanol in ethyl acetate.

Workup

  1. customwas removed under reduced pressure
  2. customThe residue was azeotroped twice with acetonitrile
  3. customthe crude product purified by chromatography
  4. washeluting with 0-5% methanol in ethyl acetate

Sources & evidence

ORD record
ord-f8231aed488949d49c4339c3952f52d4
Source dataset
uspto-grants-2001_04
Patent number
US06218376B1

Linked notes

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