Sodium Carbonate → 3-(2-Chlorothieno[3,2-d]pyrimidin-7-yl)benzenamine

HRID 2042208Notes

Reaction equation

HRID 2042208 reaction equation
Br[C:2]1[C:6]2[N:7]=[C:8]([Cl:11])[N:9]=[CH:10][C:5]=2[S:4][CH:3]=1.C(=O)([O-])[O-].[Na+].[Na+].[NH2:18][C:19]1[CH:20]=[C:21](B(O)O)[CH:22]=[CH:23][CH:24]=1.CC(C1C=C(C(C)C)C(C2C(P(C(C)(C)C)C(C)(C)C)=CC=CC=2)=C(C(C)C)C=1)C>O1CCOCC1>[Cl:11][C:8]1[N:9]=[CH:10][C:5]2[S:4][CH:3]=[C:2]([C:23]3[CH:24]=[C:19]([NH2:18])[CH:20]=[CH:21][CH:22]=3)[C:6]=2[N:7]=1

Participants

6

Reactant 4

HCID 10340Sodium CarbonateHCID 922693-Aminophenylboronic acidHCID 11618717Di-tert-butyl(2',4',6'-tris(propan-2-yl)-(1,1'-biphenyl)-2-yl)phosphaneHCID 569657247-Bromo-2-chlorothieno(3,2-d)pyrimidine

Product 1

HCID 866732143-(2-Chlorothieno[3,2-d]pyrimidin-7-yl)benzenamineYield 73.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

7-Bromo-2-chlorothieno[3,2-d]pyrimidine (3.645 g, 14.61 mmol) was dissolved in dioxane (44 mL) and 2.0 N sodium carbonate (22 mL, 43.83 mmol) and 3-aminophenylboronic acid (2 g, 14.61 mmol) were added. After flowing nitrogen to the mixture solution for 10 minutes, Pd2(PPh3)Cl2 (615 mg, 0.88 mmol) and t-ButylXphos (558 mg, mmol) were added. The reaction mixture solution was stirred at 90° C. for 6 hours and filtered with celite. The filtrate was diluted with ethyl acetate and washed with brine. The organic layer was concentrated by drying with magnesium sulfate. Purification by chromatography (20% ethyl acetate/hexane) yielded the target compound (2.8 g, 73% yield).

Workup

  1. customfor 10 minutes
  2. filtrationfiltered with celite
  3. additionThe filtrate was diluted with ethyl acetate
  4. washwashed with brine
  5. concentrationThe organic layer was concentrated
  6. dry with materialby drying with magnesium sulfate
  7. customPurification by chromatography (20% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-ef7788220f304c0fac7e0b4d7d0882f0
Source dataset
uspto-grants-2013_11
Patent number
US08586580B2

Reaction notes

Loading…