Sodium Carbonate → HCID 9878726, compound

HRID 1977407Notes

Reaction equation

HRID 1977407 reaction equation
Cl[C:2]1[C:3]2[CH:10]=[C:9]([CH2:11][CH3:12])[S:8][C:4]=2[N:5]=[CH:6][N:7]=1.[NH2:13][C:14]1[S:15][C:16]([CH3:19])=[N:17][N:18]=1.C(=O)([O-])[O-].[Na+].[Na+].C(=O)([O-])[O-].[Cs+].[Cs+]>C(O)(C)C>[CH2:11]([C:9]1[S:8][C:4]2[N:5]=[CH:6][N:7]=[C:2]([NH:13][C:14]3[S:15][C:16]([CH3:19])=[N:17][N:18]=3)[C:3]=2[CH:10]=1)[CH3:12]

Participants

6

Reactant 4

HCID 10340Sodium CarbonateHCID 10796Cesium carbonateHCID 669491,3,4-Thiadiazole, 2-amino-5-methyl-HCID 9161764-chloro-6-ethylthieno[2,3-d]pyrimidine

Product 1

HCID 9878726HCID 9878726, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A solution of Example 1C (0.20 g, 1.01 mmol) in isopropanol (2 mL) was treated with 2-amino-5-methyl-1,3,4-thiadiazole (0.115 g, 1.726 mmol) and sodium carbonate (0.18 g, 1.7 mmol), stirred at room temperature for 48 hours, treated with cesium carbonate (0.55 g, 1.7 mmol), stirred at reflux for 24 hours, concentrated, treated with water, and extracted with dichloromethane. The extract was dried (MgSO4), filtered, and concentrated. The residue was recrystallized with ethanol/water to provide the title compound.

Workup

  1. stirringstirred
  2. temperatureat reflux for 24 hours
  3. concentrationconcentrated
  4. additiontreated with water
  5. extractionextracted with dichloromethane
  6. dry with materialThe extract was dried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was recrystallized with ethanol/water

Sources & evidence

ORD record
ord-4c6f8df92bb24c5896656ac64119b5bc
Source dataset
uspto-grants-2001_05
Patent number
US06232320B1

Reaction notes

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