Acetic Acid → 6-benzyl-5-propyl[1,3]thiazolo[5,4-d]pyrimidin-7(6H)-one

HRID 855505Notes

Reaction equation

HRID 855505 reaction equation
[NH2:1][C:2]1[S:6][CH:5]=[N:4][C:3]=1[C:7]([O:9]CC)=O.[C:12](OC)(OC)(OC)[CH2:13][CH2:14][CH3:15].C(O)(=O)C.[CH2:26]([NH2:33])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>C(O)C>[CH2:26]([N:33]1[C:7](=[O:9])[C:3]2[N:4]=[CH:5][S:6][C:2]=2[N:1]=[C:12]1[CH2:13][CH2:14][CH3:15])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 7504BenzylamineHCID 1235121,1,1-TrimethoxybutaneHCID 12620181Ethyl 5-amino-1,3-thiazole-4-carboxylate

Product 1

HCID 589354496-benzyl-5-propyl[1,3]thiazolo[5,4-d]pyrimidin-7(6H)-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of ethyl 5-amino-1,3-thiazole4-carboxylate (prepared by the method of Golankiewicz and Januszczyk Tetrahedron 1985, 41, 5989-5994, 1 equiv), trimethyl orthobutyrate (2 equiv) and acetic acid (0.1 equiv) is heated at 90° C. for 3 h. Excess trimethyl orthobutyrate is removed by distillation. The residue is added to a solution of benzylamine (4.2 g, 40 mmol, 2 equiv) in ethanol (25 mL), and the resulting solution is heated at reflux for 18 h, then cooled and concentrated. The residue is triturated with EtOAc to provide 6-benzyl-5-propyl[1,3]thiazolo[5,4-d]pyrimidin-7(6H)-one (1-1).

Workup

  1. customExcess trimethyl orthobutyrate is removed by distillation
  2. temperaturethe resulting solution is heated
  3. temperatureat reflux for 18 h
  4. temperaturecooled
  5. concentrationconcentrated
  6. customThe residue is triturated with EtOAc

Sources & evidence

ORD record
ord-b908722e6faf497a989c23ea7ab46e92
Source dataset
uspto-grants-2007_08
Patent number
US07262187B2

Reaction notes

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