5-Bromo-2,4-dichloropyrimidine → 4-(5-Bromo-2-chloropyrimidin-4-yl)-3,5-dimethylisoxazole

HRID 1893397Notes

Reaction equation

HRID 1893397 reaction equation
[Br:1][C:2]1[C:3](Cl)=[N:4][C:5]([Cl:8])=[N:6][CH:7]=1.[CH3:10][C:11]1[C:15]([Sn](CCCC)(CCCC)CCCC)=[C:14]([CH3:29])[O:13][N:12]=1>CN(C=O)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Br:1][C:2]1[C:3]([C:15]2[C:11]([CH3:10])=[N:12][O:13][C:14]=2[CH3:29])=[N:4][C:5]([Cl:8])=[N:6][CH:7]=1

Participants

5

Reactant 2

HCID 2899735-Bromo-2,4-dichloropyrimidineHCID 150622153,5-Dimethyl-4-(tributylstannyl)isoxazole

Product 1

HCID 585152784-(5-Bromo-2-chloropyrimidin-4-yl)-3,5-dimethylisoxazoleYield 73.1%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

To a degassed with argon solution of 5-bromo-2,4-dichloropyrimidine (228 mg, 1.0 mmol) and 3,5-dimethyl-4-(tributylstannyl)isoxazole (772 mg, 2.0 mmol) in anhydrous DMF (2 mL), was added Pd(PPh3)2Cl2 (35 mg, 1.04 mmol). The mixture was stirred at 70° C. for 16.5 h. DMF was evaporated. The resulting orange oil was purified on ISCO (hexane/ethyl acetate gradient, 5-25%) to give the title compound (211 mg, 73.0%). 1HNMR (CDCl3): 8.81 (s, 1H), 2.44 (s, 3H), 2.30 (s, 3H). MS (ESI) m/z: Found: 288.0 (M++1), 290.0 (M++3), Calc. 286.9 (M+).

Workup

  1. customDMF was evaporated
  2. customThe resulting orange oil was purified on ISCO (hexane/ethyl acetate gradient, 5-25%)

Sources & evidence

ORD record
ord-70879c3e9f344456aebc0951010834c6
Source dataset
uspto-grants-2013_08
Patent number
US08513242B2

Reaction notes

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