Cesium carbonate → 2-Chloro-4-(3-nitrophenoxy)thieno[3,2-d]pyrimidine

HRID 526054Notes

Reaction equation

HRID 526054 reaction equation
[Cl:1][C:2]1[N:3]=[C:4](Cl)[C:5]2[S:10][CH:9]=[CH:8][C:6]=2[N:7]=1.[N+:12]([C:15]1[CH:16]=[C:17]([OH:21])[CH:18]=[CH:19][CH:20]=1)([O-:14])=[O:13].C(=O)([O-])[O-].[Cs+].[Cs+]>>[Cl:1][C:2]1[N:3]=[C:4]([O:21][C:17]2[CH:18]=[CH:19][CH:20]=[C:15]([N+:12]([O-:14])=[O:13])[CH:16]=2)[C:5]2[S:10][CH:9]=[CH:8][C:6]=2[N:7]=1

Participants

4

Reactant 3

HCID 10796Cesium carbonateHCID 111373-NitrophenolHCID 127128322,4-Dichlorothieno[3,2-d]pyrimidine

Product 1

HCID 866828282-Chloro-4-(3-nitrophenoxy)thieno[3,2-d]pyrimidineYield 91.8%

Procedure

The compound (2.9 g, 14.2 mmol) obtained in Step 2 was dissolved in N,N-dimethylsulfoneamide (70 mL), and 3-nitrophenol (1.9 g, 14.2 mmol) and cesium carbonate (9.2 g, 28.4 mmol) were added thereto, followed by stirring room temperature for 1 hour. After the reaction was complete, distilled water was added to the reaction mixture, and the resulting solid was filtered under a reduced pressure with washing with distilled water. The resulting solid was dried under a reduced pressure to obtain the title compound (yield: 4.0 g, 91.8%).

Workup

  1. additionwere added
  2. distillationdistilled water
  3. additionwas added to the reaction mixture
  4. filtrationthe resulting solid was filtered under a reduced pressure
  5. washwith washing with distilled water
  6. customThe resulting solid was dried under a reduced pressure

Sources & evidence

ORD record
ord-2394f214ba16426e87363baf4a14e18a
Source dataset
uspto-grants-2016_05
Patent number
US09345719B2

Reaction notes

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