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

HRID 2401166Notes

Reaction equation

HRID 2401166 reaction equation
[Br:1][C:2]1[C:3]([NH2:14])=[N:4][C:5]([N:9]2[CH:13]=[CH:12][CH:11]=[N:10]2)=[N:6][C:7]=1Cl.[C:15]1([SH:21])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C([O-])([O-])=O.[Cs+].[Cs+].O>C1COCC1>[Br:1][C:2]1[C:3]([NH2:14])=[N:4][C:5]([N:9]2[CH:13]=[CH:12][CH:11]=[N:10]2)=[N:6][C:7]=1[S:21][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7969ThiophenolHCID 10796Cesium carbonateHCID 866770175-bromo-6-chloro-2-(1H-pyrazol-1-yl)pyrimidin-4-amine2×

Product 1

HCID 574072415-bromo-6-(phenylthio)-2-(1H-pyrazol-1-yl)pyrimidin-4-amine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 0.1 g (0.36 mmol) of 5-bromo-6-chloro-2-(1H-pyrazol-1-yl)pyrimidin-4-amine (Intermediate 5) in 4 ml of THF, 74 μl (0.73 mmol) of thiophenol and 0.178 g (0.55 mmol) of Cs2CO3 were added. The mixture was allowed to react under microwave conditions 15 min. at 100° C. Afterwards the reaction mixture was put on 10 ml of cool water. The formed white precipitate was filtered, washed several times with cold water and dried.

Workup

  1. customto react under microwave conditions 15 min. at 100° C
  2. filtrationThe formed white precipitate was filtered
  3. washwashed several times with cold water
  4. customdried

Sources & evidence

ORD record
ord-3e7636f6b0f44df19073227f73ac74c2
Source dataset
uspto-grants-2014_08
Patent number
US08796284B2

Reaction notes

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