Potassium Carbonate → HCID 18186478, compound

HRID 1357549Notes

Reaction equation

HRID 1357549 reaction equation
[Br:1][C:2]1[CH:16]=[CH:15][C:5]([NH:6][C:7]2[C:12]([Cl:13])=[CH:11][N:10]=[C:9]([Cl:14])[N:8]=2)=[CH:4][CH:3]=1.[F:17][C:18]([F:24])([F:23])[CH2:19][CH2:20][CH2:21]Br.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Br:1][C:2]1[CH:16]=[CH:15][C:5]([N:6]([C:7]2[C:12]([Cl:13])=[CH:11][N:10]=[C:9]([Cl:14])[N:8]=2)[CH2:21][CH2:20][CH2:19][C:18]([F:24])([F:23])[F:17])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 5210064-Bromo-1,1,1-trifluorobutaneHCID 18186451HCID 18186451, compound

Product 1

HCID 18186478HCID 18186478, compoundYield 43.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-(4-bromoanilino)-2,5-dichloropyrimidine (Method 24; 315 mg, 1.0 mmol), 4,4,4-trifluoro-1-bromobutane (228 mg, 1.20 mmol) and potassium carbonate (165 mg, 1.20 mmol) in DMF (3 ml) was stirred at room temperature for 12 hours. Silica (2.5 g) was added and volatile material was removed by evaporation. The residue was purified by column chromatography, eluting with 0-40% ethyl acetate in isohexane, to give the product (187 mg). NMR: (373K); 1.84 (m, 2H), 2.28 (m, 2H), 3.99 (t, 2H), 7.22 (d, 2H), 7.58 (d, 2H), 8.23 (s, 1H); MS (MH+): 428.2, 430.2, 432.2.

Workup

  1. additionSilica (2.5 g) was added
  2. customvolatile material was removed by evaporation
  3. customThe residue was purified by column chromatography
  4. washeluting with 0-40% ethyl acetate in isohexane

Sources & evidence

ORD record
ord-b0d9347ceeaf41f8a062f4923ef66743
Source dataset
uspto-grants-2003_07
Patent number
US06593326B1

Reaction notes

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