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

HRID 324452Notes

Reaction equation

HRID 324452 reaction equation
[CH2:1]([C:3]1[S:4][C:5]2[CH:12]=[CH:11][C:10]3[CH:13]=[C:14]([CH3:17])[CH:15]=[CH:16][C:9]=3[CH:8](O)[C:6]=2[N:7]=1)[CH3:2].[NH:19]1[CH:26]=[CH:25][C:23](=[O:24])[NH:22][C:20]1=[O:21]>C(O)(=O)C>[CH2:1]([C:3]1[S:4][C:5]2[CH:12]=[CH:11][C:10]3[CH:13]=[C:14]([CH3:17])[CH:15]=[CH:16][C:9]=3[CH:8]([C:25]3[C:23](=[O:24])[NH:22][C:20](=[O:21])[NH:19][CH:26]=3)[C:6]=2[N:7]=1)[CH3:2]

Participants

4

Reactant 2

HCID 1174UracilHCID 70115187HCID 70115187, compound

Product 1

HCID 70113478(+/-)-5-(2-Ethyl-7-methyl-4H-benzo[5,6]cyclohepta[1,2-d]thiazol-4-yl)-2,4(1H,3H)-pyrimidinedione

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

A solution of the product from step (iii) (785 mg) in acetic acid (5 ml) was added to a suspension of uracil (0.673 g) in acetic acid (25 ml) at 90° C. over 3 min. After 1.5 h the solvent was removed under reduced pressure and the residue partitioned between ethyl acetate and water. The organic phase was washed with water, dried (MgSO4) and evaporated under reduced pressure. Purification was by chromatography eluting with ethyl acetate.

Workup

  1. customAfter 1.5 h the solvent was removed under reduced pressure
  2. customthe residue partitioned between ethyl acetate and water
  3. washThe organic phase was washed with water
  4. dry with materialdried (MgSO4)
  5. customevaporated under reduced pressure
  6. customPurification
  7. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-973fc0b49a414941a053347a6e0c04cf
Source dataset
uspto-grants-2001_04
Patent number
US06218376B1

Reaction notes

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