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

HRID 324468

Reaction equation

HRID 324468 reaction equation
[CH3:1][N:2]1[CH:9]=[CH:8][C:6](=[O:7])[NH:5][C:3]1=[O:4].[CH3:10][C:11]1[S:12][C:13]2[CH:20]=[CH:19][C:18]3[CH:21]=[C:22]([CH2:25][CH2:26][CH3:27])[CH:23]=[CH:24][C:17]=3[CH:16](O)[C:14]=2[N:15]=1>C(O)(=O)C>[CH3:1][N:2]1[CH:9]=[C:8]([CH:16]2[C:14]3[N:15]=[C:11]([CH3:10])[S:12][C:13]=3[CH:20]=[CH:19][C:18]3[CH:21]=[C:22]([CH2:25][CH2:26][CH3:27])[CH:23]=[CH:24][C:17]2=3)[C:6](=[O:7])[NH:5][C:3]1=[O:4]

Participants

4

Reactant 2

HCID 120091-MethyluracilHCID 70112533(+/-)-2-Methyl-7-n-propyl-4H-benzo[5,6]cyclohepta[1,2-d]thiazol-4-ol

Product 1

HCID 70115254(+/-)-1-Methyl-5-(2-methyl-7-n-propyl-4H-benzo[5,6]cyclohepta[1,2-d]thiazol-4-yl)-2,4-(1H,3H)-pyrimidinedione

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of the 1-methyluracil (0.5 g) and the product from step (xi) in acetic acid (50 ml) was heated at reflux 2 h. The solvent was removed under reduced pressure and the residue partitioned between ethyl acetate/water. The organic layer collected and dried over MgSO4. The solvent evaporated and the crude product purified by flash chromatography eluting with ethyl acetate.

Workup

  1. temperatureat reflux 2 h
  2. customThe solvent was removed under reduced pressure
  3. customthe residue partitioned between ethyl acetate/water
  4. customThe organic layer collected
  5. dry with materialdried over MgSO4
  6. customThe solvent evaporated
  7. customthe crude product purified by flash chromatography
  8. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-f8bee6b99aaa4484b4d79496ff0e3701
Source dataset
uspto-grants-2001_04
Patent number
US06218376B1

Linked notes

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