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

HRID 324493Notes

Reaction equation

HRID 324493 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][O-:27].[Na+]>>[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]([O:27][CH3:26])[S:3][C:4]=3[CH:11]=[CH:10][C:9]=2[CH:12]=1

Participants

3

Reactant 2

HCID 10942334Sodium MethoxideHCID 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 70112888(+/-)-5-(7-Chloro-2-methoxy-4H-benzo[5,6]cyclohepta[1,2-d]thiazol-4-yl)-1-methyl-2,4(1H,3H)-pyrimidinedione

Procedure

The product from example 44 step (viii) (0.1 g) was heated with a solution of sodium methoxide (made from sodium (0.2 g) in dry methanol (10 ml)) at reflux for 3 h. The mixture was partitioned between ethyl acetate and water. The organic phase was collected, dried (MgSO4) and solvent evaporated under reduced pressure. Purification was by chromatography eluting with 70% ethyl acetate in isohexane to give the title product as a colourless solid.

Workup

  1. temperatureat reflux for 3 h
  2. customThe mixture was partitioned between ethyl acetate and water
  3. customThe organic phase was collected
  4. dry with materialdried (MgSO4) and solvent
  5. customevaporated under reduced pressure
  6. customPurification
  7. washeluting with 70% ethyl acetate in isohexane

Sources & evidence

ORD record
ord-21bdb3aea67b4e769618dc153de41058
Source dataset
uspto-grants-2001_04
Patent number
US06218376B1

Reaction notes

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