HCID 11495566, compound → HCID 11646895, compound

HRID 2102367Notes

Reaction equation

HRID 2102367 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:16]3[C:15]([O:17][CH2:18][CH2:19][CH2:20][O:21][C:22]4[CH:27]=[CH:26][CH:25]=[C:24]([N+:28]([O-])=O)[CH:23]=4)=[N:14][CH:13]=[N:12][C:11]=3[S:10][CH:9]=2)=[CH:4][CH:3]=1.[H][H]>O1CCCC1.CO.C(O)(=O)C.[Pd]>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:16]3[C:15]([O:17][CH2:18][CH2:19][CH2:20][O:21][C:22]4[CH:23]=[C:24]([CH:25]=[CH:26][CH:27]=4)[NH2:28])=[N:14][CH:13]=[N:12][C:11]=3[S:10][CH:9]=2)=[CH:4][CH:3]=1

Participants

7

Reactant 2

HCID 11495566HCID 11495566, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 11646895HCID 11646895, compoundYield 77.4%

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

5-(4-Fluorophenyl)-4-[3-(3-nitrophenoxy)propoxy]thieno[2,3-d]pyrimidine (250 mg, 0.588 mmol) was dissolved in tetrahydrofuran (15 mL) and added (under an atmosphere of argon) to a suspension of 25 mg of 10% palladium/carbon in methanol (30 mL) and acetic acid (5 mL). The mixture was then shaken under 40 psi of hydrogen overnight. The palladium/carbon was removed by filtration and the filtrate was concentrated in vacuo. The residue was dissolved in ethyl acetate (50 mL) and washed with aqueous sodium bicarbonate solution (2×30 mL). The organic layer was separated, concentrated, and purified by column chromatography over silica gel using 33% ethyl acetate in hexanes as eluant to give 180 mg (76%) of 3-(3-{[5-(4-fluorophenyl)thieno[2,3-d]pyrimidin-4-yl]oxy}propoxy)aniline as a colorless gum. MS [M+H] 396.1, 1H NMR (CDCl3) δ (ppm) 8.65 (s, 1H), 7.45-7.40 (m, 2H), 7.21 (s, 1H), 7.09-7.00 (m, 3H), 6.30 (d, J=2.1 Hz, 1H), 6.20 (d, J=2.8 Hz, 1H), 6.11 (s, 1H), 4.58 (t, J=6.0 Hz, 2H), 3.69 (t, J=6.0 Hz, 3H), 3.68 (b, 2H), 2.05 (m, 2H).

Workup

  1. additionadded (under an atmosphere of argon)
  2. customThe palladium/carbon was removed by filtration
  3. concentrationthe filtrate was concentrated in vacuo
  4. dissolutionThe residue was dissolved in ethyl acetate (50 mL)
  5. washwashed with aqueous sodium bicarbonate solution (2×30 mL)
  6. customThe organic layer was separated
  7. concentrationconcentrated
  8. custompurified by column chromatography over silica gel using 33% ethyl acetate in hexanes as eluant

Sources & evidence

ORD record
ord-1f7ff996e1104bbf8278f50ecbad290b
Source dataset
uspto-grants-2009_08
Patent number
US07576080B2

Reaction notes

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