Nitrogen → HCID 67328114, compound

HRID 1464977Notes

Reaction equation

HRID 1464977 reaction equation
Br[C:2]1[C:6]2[N:7]=[CH:8][N:9]=[C:10]([NH2:11])[C:5]=2[S:4][CH:3]=1.N#N.[CH2:14]([Sn](CCCC)(CCCC)C=C)[CH2:15]CC.[F-].[K+]>O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH:14]([C:2]1[C:6]2[N:7]=[CH:8][N:9]=[C:10]([NH2:11])[C:5]=2[S:4][CH:3]=1)=[CH2:15]

Participants

7

Reactant 4

HCID 947NitrogenHCID 81998TributylvinyltinHCID 522689Potassium FluorideHCID 673608657-Bromothieno[3,2-d]pyrimidin-4-amine

Product 1

HCID 67328114HCID 67328114, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
120 °C

Procedure

7-Bromothieno[3,2-d]pyrimidine-4-amine (2.4 g, 10.43 mmol) was dissolved in dioxane (30 mL) and then treated with N2 gas for 20 minutes. Pd(PPh3)4 (723 mg, 0.63 mmol) and tributyl(vinyl)tin (3.35 mL, 11.5 mmol) were added thereto and stirred at 120° C. for 7 hours. The reaction mixture was cooled to room temperature, an aqueous KF solution (10%, 30 mL) was added thereto and stirred for 2 hours. The reaction mixture was filtered with Celite and washed with ethyl acetate. The aqueous layer was separated from the organic layer and extracted with ethyl acetate. The combined organic layer was dried with MgSO4 and concentrated. The resulting mixture was purified by silica gel chromatography (DCM/MeOH=95/5) to obtain the title compound having a yellow color.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. stirringstirred for 2 hours
  3. filtrationThe reaction mixture was filtered with Celite
  4. washwashed with ethyl acetate
  5. customThe aqueous layer was separated from the organic layer
  6. extractionextracted with ethyl acetate
  7. dry with materialThe combined organic layer was dried with MgSO4
  8. concentrationconcentrated
  9. customThe resulting mixture was purified by silica gel chromatography (DCM/MeOH=95/5)

Sources & evidence

ORD record
ord-a32c585d7bb54fe6891e556386981c4e
Source dataset
uspto-grants-2015_04
Patent number
US08999973B2

Reaction notes

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