Acetic Anhydride → N-[4-(3-{[5-(4-fluorophenyl)thieno[2,3-d]pyrimidin-4-yl]amino}propyl)phenyl]acetamide

HRID 2102385Notes

Reaction equation

[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][NH:11][C:12]2[C:13]3[C:20]([C:21]4[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=4)=[CH:19][S:18][C:14]=3[N:15]=[CH:16][N:17]=2)=[CH:4][CH:3]=1.[C:28](OC(=O)C)(=[O:30])[CH3:29]>C(Cl)Cl>[F:27][C:24]1[CH:23]=[CH:22][C:21]([C:20]2[C:13]3[C:12]([NH:11][CH2:10][CH2:9][CH2:8][C:5]4[CH:6]=[CH:7][C:2]([NH:1][C:28](=[O:30])[CH3:29])=[CH:3][CH:4]=4)=[N:17][CH:16]=[N:15][C:14]=3[S:18][CH:19]=2)=[CH:26][CH:25]=1

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of N-[3-(4-aminophenyl)propyl]-5-(4-fluorophenyl)thieno[2,3-d]pyrimidin-4-amine (0.014 g, 0.037 mmol) and acetic anhydride (0.01 mL) in methylene chloride (2.0 mL) was heated to 60° C. for 6 h. The reaction was allowed to cool to room temperature and concentrated in vacuo. The residue was then dissolved in ethyl acetate (30 mL) and the organic layer was washed with sodium bicarbonate (2×25 mL). Concentration, followed by followed by silica gel column chromatography purification (using 3% methanol in 1:1 ethyl acetate/hexane and ammonia (0.03%) as eluent) afforded N-[4-(3-{[5-(4-fluorophenyl)thieno[2,3-d]pyrimidin-4-yl]amino}propyl)phenyl]acetamide in 90% yield.

Workup

temperatureto cool to room temperature
concentrationconcentrated in vacuo
dissolutionThe residue was then dissolved in ethyl acetate (30 mL)
washthe organic layer was washed with sodium bicarbonate (2×25 mL)
concentrationConcentration
customby followed by silica gel column chromatography purification (using 3% methanol in 1:1 ethyl acetate/hexane and ammonia (0.03%) as eluent)

Sources & evidence

ORD record: ord-84c5fcf6298042f5818ffb76e573df77
Source dataset: uspto-grants-2009_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07576080B2

Reaction notes

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