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

HRID 324494Notes

Reaction equation

HRID 324494 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.[NH3:26]>C(O)C>[NH2:26][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

Participants

4

Reactant 2

HCID 222AmmoniaHCID 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 86756618(+/-)-5-(2-Amino-7-chloro-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 0.88 ammonia (2 ml) and ethanol (1 ml) in a sealed tube at 100° C. for 24 h. The volatiles were removed under reduced pressure and the residue triturated with ethyl acetate and methanol mixtures to leave the title product as a yellow solid.

Workup

  1. customThe volatiles were removed under reduced pressure
  2. customthe residue triturated with ethyl acetate and methanol mixtures

Sources & evidence

ORD record
ord-a4f116eeb5c64d4d960b7fb42dbeac83
Source dataset
uspto-grants-2001_04
Patent number
US06218376B1

Reaction notes

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