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

HRID 324492Notes

Reaction equation

HRID 324492 reaction equation
Cl[C:2]1[S:3][C:4]2[CH:11]=[CH:10][C:9]3[CH:12]=[C:13]([Cl:16])[CH:14]=[CH:15][C:8]=3[CH:7]([C:17]3[C:18](=[O:25])[NH:19][C:20](=[O:24])[N:21]([CH3:23])[CH:22]=3)[C:5]=2[N:6]=1>C(O)(=O)C.[Zn]>[Cl:16][C:13]1[CH:14]=[CH:15][C:8]2[CH:7]([C:17]3[C:18](=[O:25])[NH:19][C:20](=[O:24])[N:21]([CH3:23])[CH:22]=3)[C:5]3[N:6]=[CH:2][S:3][C:4]=3[CH:11]=[CH:10][C:9]=2[CH:12]=1

Participants

4

Reactant 1

HCID 70113243(+/-)-5-(2,7-Dichloro-4H-benzo[5,6]cyclohepta[1,2-d]thiazol-4-yl)-1-methyl-2,4(1H,3H)-pyrimidinedione

Product 1

HCID 70113817(+/-)-5-(7-Chloro-4H-benzo[5,6]cyclohepta[1,2-d]thiazol-4-yl)-1-methyl-2,4(1H,3H)-pyrimidinedione

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

Zinc powder (4 g) was added to a solution of the product from example 44 step (viii) (0.5 g) in acetic acid. After 24 h the solvent was evaporated under reduced pressure and the residue partitioned between saturated sodium bicarbonate solution and dichloromethane. The organic phase was collected, dried, (MgSO4) and solvent evaporated to leave as a beige foam. Purification by trituration and filtration from isohexane/ethyl acetate mixtures gave the title product.

Workup

  1. customAfter 24 h the solvent was evaporated under reduced pressure
  2. customthe residue partitioned between saturated sodium bicarbonate solution and dichloromethane
  3. customThe organic phase was collected
  4. customdried
  5. custom(MgSO4) and solvent evaporated
  6. customto leave as a beige foam
  7. customPurification
  8. filtrationby trituration and filtration from isohexane/ethyl acetate mixtures

Sources & evidence

ORD record
ord-f840ebdd4cad4fa2853399986fc0c241
Source dataset
uspto-grants-2001_04
Patent number
US06218376B1

Reaction notes

Loading…