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

HRID 324496Notes

Reaction equation

HRID 324496 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.[CH3:26][NH:27][CH3:28]>C(O)C>[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]=[C:2]([N:27]([CH3:28])[CH3:26])[S:3][C:4]=3[CH:11]=[CH:10][C:9]=2[CH:12]=1

Participants

4

Reactant 2

HCID 674DimethylamineHCID 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 70113722(+/-)-5-(7-Chloro-2-dimethylamino-4H-benzo[5,6]cyclohepta[1,2-d]thiazol-4-yl)-1-methyl-2,4(1H,3H)-pyrimidinedione

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The product from example 44 step (viii) (0.05 g) was heated with 40% aq. dimethylamine (2 ml) in ethanol (1 ml) for 1 hour. The mixture was partitioned between ethyl acetate and water. The organic phase was collected, dried (MgSO4) and solvent evaporated under reduced pressure. The residue was triturated with ethyl acetate/isohexane mixtures and the title product collected by filtration as a pale yellow solid.

Workup

  1. customThe mixture was partitioned between ethyl acetate and water
  2. customThe organic phase was collected
  3. dry with materialdried (MgSO4) and solvent
  4. customevaporated under reduced pressure
  5. customThe residue was triturated with ethyl acetate/isohexane mixtures
  6. filtrationthe title product collected by filtration as a pale yellow solid

Sources & evidence

ORD record
ord-f7b1c4489fe34e21bbc6312f5fb6c4d0
Source dataset
uspto-grants-2001_04
Patent number
US06218376B1

Reaction notes

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