3-Chloro-4-(3-fluorobenzyloxy)aniline → N-{3-chloro-4-[(3-fluorobenzyl)oxy]phenyl}-5-(3-chloropropyl)-5H-pyrrolo[3,2-d]pyrimidin-4-amine

HRID 1926106Notes

Reaction equation

Cl[C:2]1[C:3]2[N:10]([CH2:11][CH2:12][CH2:13][Cl:14])[CH:9]=[CH:8][C:4]=2[N:5]=[CH:6][N:7]=1.[Cl:15][C:16]1[CH:17]=[C:18]([CH:20]=[CH:21][C:22]=1[O:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[C:27]([F:31])[CH:26]=1)[NH2:19]>C(O)(C)C>[Cl:15][C:16]1[CH:17]=[C:18]([NH:19][C:2]2[C:3]3[N:10]([CH2:11][CH2:12][CH2:13][Cl:14])[CH:9]=[CH:8][C:4]=3[N:5]=[CH:6][N:7]=2)[CH:20]=[CH:21][C:22]=1[O:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[C:27]([F:31])[CH:26]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 4-chloro-5-(3-chloropropyl)-5H-pyrrolo[3,2-d]pyrimidine (839 mg), 3-chloro-4-[(3-fluorobenzyl)oxy]aniline (1.10 g) and isopropyl alcohol (5 mL) was stirred at 80° C. for 1.5 hrs. The mixture was concentrated under reduced pressure, saturated aqueous sodium hydrogen carbonate (30 mL) was added to the residue, and the mixture was extracted with ethyl acetate (30 mL×3). The organic layers were combined, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent, hexane:ethyl acetate=90:10→20:80) to give the title compound (1.19 g).

Workup

concentrationThe mixture was concentrated under reduced pressure, saturated aqueous sodium hydrogen carbonate (30 mL)
additionwas added to the residue
extractionthe mixture was extracted with ethyl acetate (30 mL×3)
dry with materialdried over anhydrous magnesium sulfate
concentrationconcentrated under reduced pressure
customThe residue was purified by silica gel column chromatography (eluent, hexane:ethyl acetate=90:10→20:80)

Sources & evidence

ORD record: ord-86845efe53ba4349ae506b03ed20db0c
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08178543B2

Reaction notes

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