Cesium fluoride → HCID 53468867, compound

HRID 2401171Notes

Reaction equation

HRID 2401171 reaction equation
Br[C:2]1[C:3]([NH2:18])=[N:4][C:5]([N:13]2[CH:17]=[CH:16][CH:15]=[N:14]2)=[N:6][C:7]=1[N:8]1[CH:12]=[CH:11][CH:10]=[N:9]1.[F-].[Cs+].C([Sn](CCCC)(CCCC)[C:26]1[S:27][CH:28]=[CH:29][N:30]=1)CCC>>[N:13]1([C:5]2[N:4]=[C:3]([NH2:18])[C:2]([C:26]3[S:27][CH:28]=[CH:29][N:30]=3)=[C:7]([N:8]3[CH:12]=[CH:11][CH:10]=[N:9]3)[N:6]=2)[CH:17]=[CH:16][CH:15]=[N:14]1

Participants

4

Reactant 3

HCID 25953Cesium fluorideHCID 27632592-(Tributylstannyl)-1,3-thiazoleHCID 534669585-bromo-2,6-di(1H-pyrazol-1-yl)pyrimidin-4-amine

Product 1

HCID 53468867HCID 53468867, compoundYield 47.2%

Conditions

Temperature
80 °C

Procedure

A mixture of 8.9 mg (13.1 μmol) of Pd-PEPPSI-IPr-catalyst, 0.1 g (0.33 mmol) of 5-bromo-2,6-di(1H-pyrazol-1-yl)pyrimidin-4-amine (Example 1), 0.1 g (0.65 mmol) of cesium fluoride and activated, crushed 4 Å molecular sieves (33 mg) in a glass vial was purged with argon and 1 ml of dioxane was added. 0.15 (0.39 mmol) of 2-tributylstannylthiazole was then added and the reaction was stirred at 80° C. for 24 h. The mixture was filtered throw celite/CsF. The solvent was removed in vacuum. The residue was purified by column chromatography with silica gel and methylene chloride and methanol as eluent to give 47.9 mg (47.2%) of the desired product.

Workup

  1. customcrushed 4 Å molecular sieves (33 mg) in a glass vial
  2. customwas purged with argon and 1 ml of dioxane
  3. additionwas added
  4. filtrationThe mixture was filtered throw celite/CsF
  5. customThe solvent was removed in vacuum
  6. customThe residue was purified by column chromatography with silica gel and methylene chloride and methanol as eluent

Sources & evidence

ORD record
ord-77dc0686a6574e82ada8cd11b67837d1
Source dataset
uspto-grants-2014_08
Patent number
US08796284B2

Reaction notes

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