N-methyl-2-pyrrolidone → 6-(2-furyl)-N-{3-methyl-4-[(6-methylpyridin-3-yl)oxy]phenyl}-5H-pyrrolo[3,2-d]pyrimidin-4-amine

HRID 1786933Notes

Reaction equation

HRID 1786933 reaction equation
Cl[C:2]1[C:3]2[NH:10][C:9]([C:11]3[O:12][CH:13]=[CH:14][CH:15]=3)=[CH:8][C:4]=2[N:5]=[CH:6][N:7]=1.[CH3:16][C:17]1[CH:18]=[C:19]([CH:21]=[CH:22][C:23]=1[O:24][C:25]1[CH:26]=[N:27][C:28]([CH3:31])=[CH:29][CH:30]=1)[NH2:20].CN1CCCC1=O.C(=O)([O-])O.[Na+]>O>[O:12]1[CH:13]=[CH:14][CH:15]=[C:11]1[C:9]1[NH:10][C:3]2[C:2]([NH:20][C:19]3[CH:21]=[CH:22][C:23]([O:24][C:25]4[CH:26]=[N:27][C:28]([CH3:31])=[CH:29][CH:30]=4)=[C:17]([CH3:16])[CH:18]=3)=[N:7][CH:6]=[N:5][C:4]=2[CH:8]=1

Participants

6

Reactant 4

HCID 13387N-methyl-2-pyrrolidoneHCID 516892Sodium BicarbonateHCID 114244343-Methyl-4-((6-methylpyridin-3-yl)oxy)anilineHCID 713033474-chloro-6-(furan-2-yl)-5H-pyrrolo[3,2-d]pyrimidine

Product 1

HCID 575971966-(2-furyl)-N-{3-methyl-4-[(6-methylpyridin-3-yl)oxy]phenyl}-5H-pyrrolo[3,2-d]pyrimidin-4-amineYield 57.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 4-chloro-6-(2-furyl)-5H-pyrrolo[3,2-d]pyrimidine (110 mg), 3-methyl-4-[(6-methylpyridin-3-yl)oxy]aniline (161 mg) and 1-methyl-2-pyrrolidinone (2.5 mL) was stirred at 140° C. for 2 hrs, poured into water (10 mL) and adjusted to pH 8 with saturated aqueous sodium hydrogen carbonate. The mixture was extracted with ethyl acetate (25 mL×2) and the organic layers were combined and dried over anhydrous magnesium sulfate. After concentration under reduced pressure, the residue was subjected to silica gel column chromatography (eluent, hexane:ethyl acetate=1:1→0:1). The object fraction was concentrated under reduced pressure. Chloroform-diisopropyl ether was added to the residue, and the solid was collected by filtration and dried under reduced pressure at 60° C. to give the title compound (114 mg).

Workup

  1. extractionThe mixture was extracted with ethyl acetate (25 mL×2)
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationAfter concentration under reduced pressure
  4. concentrationThe object fraction was concentrated under reduced pressure
  5. additionChloroform-diisopropyl ether was added to the residue
  6. filtrationthe solid was collected by filtration
  7. customdried under reduced pressure at 60° C.

Sources & evidence

ORD record
ord-12d14ab5c17b4725aa3770f42c1b9592
Source dataset
uspto-grants-2009_03
Patent number
US07507740B2

Reaction notes

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