4-Chloro-5-(4-fluorophenyl)thieno(2,3-d)pyrimidine → 4-But-3-en-1-yl-5-(4-fluorophenyl)thieno[2,3-d]pyrimidine

HRID 2102382Notes

Reaction equation

HRID 2102382 reaction equation
[CH2:1]([Mg]Br)[CH2:2][CH:3]=[CH2:4].Cl[C:8]1[C:9]2[C:16]([C:17]3[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=3)=[CH:15][S:14][C:10]=2[N:11]=[CH:12][N:13]=1>O1CCCC1.[Cu]I>[CH2:1]([C:8]1[C:9]2[C:16]([C:17]3[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=3)=[CH:15][S:14][C:10]=2[N:11]=[CH:12][N:13]=1)[CH2:2][CH:3]=[CH2:4]

Participants

5

Reactant 2

HCID 27829114-Chloro-5-(4-fluorophenyl)thieno(2,3-d)pyrimidineHCID 178418797HCID 178418797, compound

Product 1

HCID 116233584-But-3-en-1-yl-5-(4-fluorophenyl)thieno[2,3-d]pyrimidineYield 67%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 8028TetrahydrofuranSolvent

Procedure

3-Butenylmagnesium bromide (0.0040 mol) was added to a solution of 4-chloro-5-(4-fluorophenyl)thieno[2,3-d]pyrimidine (0.529 g, 0.00200 mol), copper (I) iodide (0.038 g, 0.00020 mol) and ferrous bromide (0.043 g, 0.00020 mol) in tetrahydrofuran (10 mL) and the resulting mixture was maintained at room temperature for 5 h, then quenched by the addition of water (10 mL). Ethyl acetate (50 mL) was added and the mixture was filtered. The filtrate was washed with a saturated solution of sodium bicarbonate (40 mL) and the organics were concentrated and purified by silica gel column chromatography (using 15% ethyl acetate/hexane as eluent) to afford 4-But-3-en-1-yl-5-(4-fluorophenyl)thieno[2,3-d]pyrimidine as a white solid in 67% yield.

Workup

  1. customquenched by the addition of water (10 mL)
  2. additionEthyl acetate (50 mL) was added
  3. filtrationthe mixture was filtered
  4. washThe filtrate was washed with a saturated solution of sodium bicarbonate (40 mL)
  5. concentrationthe organics were concentrated
  6. custompurified by silica gel column chromatography (using 15% ethyl acetate/hexane as eluent)

Sources & evidence

ORD record
ord-344f859d58d44ae0b5925136d8772ea9
Source dataset
uspto-grants-2009_08
Patent number
US07576080B2

Reaction notes

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