5-Bromopyrimidine → HCID 22143524, compound

HRID 985233Notes

Reaction equation

HRID 985233 reaction equation
Br[C:2]1[CH:3]=[N:4][CH:5]=[N:6][CH:7]=1.[Cl:8][C:9]1[CH:14]=[CH:13][N:12]=[C:11]2[CH:15]=[C:16]([Sn](C)(C)C)[S:17][C:10]=12>C1(C)C=CC=CC=1>[Cl:8][C:9]1[CH:14]=[CH:13][N:12]=[C:11]2[CH:15]=[C:16]([C:2]3[CH:3]=[N:4][CH:5]=[N:6][CH:7]=3)[S:17][C:10]=12

Participants

4

Reactant 2

HCID 783445-BromopyrimidineHCID 221434977-Chloro-2-(trimethylstannyl)thieno[3,2-b]pyridine

Product 1

HCID 22143524HCID 22143524, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Tereakis(triphenylphosphine)palladium (17 mg) was added to a solution of 5-bromopyrimidine (0.057 g, 0.36 mmole) and 7-chloro-2-(trimethylstannyl)thieno[3,2-b]pyridine 39a (0.119 g, 0.36 mmole) in toluene (10 ml). The reaction mixture was stirred at 90□ C. overnight. After cooling to room temperature, the mixture was filtered, washed with CH2Cl2 and was partitioned between H2O (20 ml) and CH2Cl2 (2×20 ml). The combined organic layers were dried over MgSO4 and concentrated. The residue was purified by flash column chromatography eluting with 0-1% MeOH in CH2Cl2 to give white solid (0.045 g, 51%); 1H NMR (300 MHz, C6D6) δ9.25 (1H, s), 9.10 (2H, s), 8.64 (1H, d, J=5.1 Hz), 7.89 (1H, s), 7.34 (1H, d, J=5.1 Hz); ESIMS (MH+): 248.00.

Workup

  1. customovernight
  2. filtrationthe mixture was filtered
  3. washwashed with CH2Cl2
  4. customwas partitioned between H2O (20 ml) and CH2Cl2 (2×20 ml)
  5. dry with materialThe combined organic layers were dried over MgSO4
  6. concentrationconcentrated
  7. customThe residue was purified by flash column chromatography
  8. washeluting with 0-1% MeOH in CH2Cl2

Sources & evidence

ORD record
ord-f16684535e6249cba683877e83c35811
Source dataset
uspto-grants-2005_03
Patent number
US06869962B2

Reaction notes

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