Water → 5-bromo-6-chloro-2-(1H-pyrazol-1-yl)pyrimidin-4-amine

HRID 2401163Notes

Reaction equation

HRID 2401163 reaction equation
[Br:1][C:2]1[C:3]([NH2:12])=[N:4][C:5](S(C)=O)=[N:6][C:7]=1[Cl:8].[NH:13]1[CH:17]=[CH:16][CH:15]=[N:14]1.C(=O)([O-])[O-].[Cs+].[Cs+].O>CN(C=O)C>[Br:1][C:2]1[C:3]([NH2:12])=[N:4][C:5]([N:13]2[CH:17]=[CH:16][CH:15]=[N:14]2)=[N:6][C:7]=1[Cl:8]

Participants

6

Reactant 4

HCID 962WaterHCID 1048PyrazoleHCID 10796Cesium carbonateHCID 866770165-Bromo-6-chloro-2-methanesulfinylpyrimidin-4-amine2×

Product 1

HCID 866770175-bromo-6-chloro-2-(1H-pyrazol-1-yl)pyrimidin-4-amineYield 65%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1 g (3.7 mmol) of 5-bromo-6-chloro-2-(methylsulfinyl)pyrimidine-4-amine (intermediate 2) was suspended in 10 ml of DMF. To this suspension were added 0.33 g (4.8 mmol) de pyrazole and 0.8 g of cesium carbonate. The reaction mixture was turned immediately light yellow color and allowed to stir at room temperature for about 1 to 2 hours. After nearly complete conversion to the corresponding monosubstituted derivative as was indicated by TLC the solution was poured onto 100 ml of cool water. The formed precipitated was filtered, washed with water and dried to afford 0.66 g (65%) of the desired product.

Workup

  1. customThe formed precipitated
  2. filtrationwas filtered
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-be51a176488d42638229ef21fd1ee146
Source dataset
uspto-grants-2014_08
Patent number
US08796284B2

Reaction notes

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