Ammonia → HCID 86642107, compound

HRID 1943218Notes

Reaction equation

HRID 1943218 reaction equation
[CH2:1]([O:3][C:4](=[O:15])[CH2:5][S:6][C:7]1[C:8](Cl)=[N:9][C:10]([Cl:13])=[N:11][CH:12]=1)[CH3:2].[NH3:16].C(O)(C)C>CN(C=O)C>[CH2:1]([O:3][C:4](=[O:15])[CH2:5][S:6][C:7]1[C:8]([NH2:16])=[N:9][C:10]([Cl:13])=[N:11][CH:12]=1)[CH3:2]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 3776IsopropanolHCID 86642108HCID 86642108, compound

Product 1

HCID 86642107HCID 86642107, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of ethyl[(2,4-dichloro-5-pyrimidinyl)thio]acetate (2.0 g, 7.49 mmol) in DMF (75 ml) was treated with ammonia in isopropanol (7.49 ml, 14.97 mmol) in a pressure tube. The tube was capped, and the reaction was stirred at ambient temperature. Upon completion, the solution was concentrated under reduced pressure and pumped on to remove any residual DMF. The crude material was chromatographed using a gradient of 0-10% acetone/chloroform. The product contained a small amount of cyclized material (which is the product of the next step). The product was isolated as a light yellow solid.

Workup

  1. customThe tube was capped
  2. concentrationUpon completion, the solution was concentrated under reduced pressure
  3. customto remove any residual DMF
  4. customThe crude material was chromatographed
  5. customThe product was isolated as a light yellow solid

Sources & evidence

ORD record
ord-0ece6670bfa44028b1c3e9016e0e6e58
Source dataset
uspto-grants-2013_03
Patent number
US08389524B2

Reaction notes

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