Dimethylformamide → HCID 178504192, compound

HRID 419726Notes

Reaction equation

HRID 419726 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[NH:8][N:9]=[C:10](I)[C:3]=12.[CH3:12][Si:13]([CH3:17])([CH3:16])[C:14]#[CH:15].CN(C=O)C.C1COCC1>C(Cl)Cl.[Cu]I.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.CC(C)=O>[Cl:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[NH:8][N:9]=[C:10]([C:15]#[C:14][Si:13]([CH3:17])([CH3:16])[CH3:12])[C:3]=12

Participants

9

Reactant 4

HCID 6228DimethylformamideHCID 8028TetrahydrofuranHCID 66111TrimethylsilylacetyleneHCID 178478397HCID 178478397, compound

Product 1

HCID 178504192HCID 178504192, compoundYield 37.5%

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418397HCID 178418397, compoundCatalystHCID 180AcetoneSolventHCID 6344DichloromethaneSolvent

Procedure

Charge 4-chloro-3-iodo-1H-pyrazolo[3,4-d]pyrimidine (5.4 g, 1.0 eq), trimethyl silyl acetylene (11.347 g, 6.0 eq), CuI (1.833 g, 0.5 eq), TEA (2.68 mL, 1.0 eq), DMF (67.5 mL), and THF (202.5 mL) in a round bottom flask under argon atmosphere. Stir the reaction mass under argon atm for 30 min. Charge (PPh3)4Pd (2.225 g, 0.1 eq) and stir the reaction mass at 35° C. for 3 h. Monitor the reaction by TLC (10% acetone in DCM). Concentrate the reaction mass under reduced pressure. Charge ethyl acetate and wash with saturated sodium bicarbonate solution, water and saturated aq. sodium chloride. Dry the organic layer over anhydrous sodium sulfate and concentrate the organic layer under reduced pressure. Purify the compound by column chromatography (silica 100-200 mesh, DCM-Acetone) to give desired product (1.81 g, 36.14%).

Workup

  1. concentrationConcentrate the reaction mass under reduced pressure
  2. washCharge ethyl acetate and wash with saturated sodium bicarbonate solution, water and saturated aq. sodium chloride
  3. dry with materialDry the organic layer over anhydrous sodium sulfate
  4. concentrationconcentrate the organic layer under reduced pressure
  5. customPurify the compound by column chromatography (silica 100-200 mesh, DCM-Acetone)

Sources & evidence

ORD record
ord-a65619109a904b64a102c571d1fccba0
Source dataset
uspto-grants-2012_01
Patent number
US08093383B2

Reaction notes

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