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

HRID 1926030Notes

Reaction equation

HRID 1926030 reaction equation
Cl[C:2]1[C:3]2[N:10]([CH3:11])[C:9]([C:12]3[O:13][CH:14]=[CH:15][CH:16]=3)=[CH:8][C:4]=2[N:5]=[CH:6][N:7]=1.[CH3:17][C:18]1[CH:19]=[C:20]([CH:22]=[CH:23][C:24]=1[O:25][C:26]1[CH:27]=[N:28][C:29]([CH3:32])=[CH:30][CH:31]=1)[NH2:21].CN1CCCC1=O.C(=O)([O-])O.[Na+]>O>[O:13]1[CH:14]=[CH:15][CH:16]=[C:12]1[C:9]1[N:10]([CH3:11])[C:3]2[C:2]([NH:21][C:20]3[CH:22]=[CH:23][C:24]([O:25][C:26]4[CH:27]=[N:28][C:29]([CH3:32])=[CH:30][CH:31]=4)=[C:18]([CH3:17])[CH:19]=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 714134594-Chloro-6-(furan-2-yl)-5-methyl-5H-pyrrolo[3,2-d]pyrimidine

Product 1

HCID 575971486-(2-furyl)-5-methyl-N-{3-methyl-4-[(6-methylpyridin-3-yl)oxy]phenyl}-5H-pyrrolo[3,2-d]pyrimidin-4-amineYield 64.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 4-chloro-6-(2-furyl)-5-methyl-5H-pyrrolo[3,2-d]pyrimidine (92 mg), 3-methyl-4-[(6-methylpyridin-3-yl)oxy]aniline (102 mg) and 1-methyl-2-pyrrolidinone (2.5 mL) was stirred at 140° C. for 3.5 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. Diethyl 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 (105 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. additionDiethyl 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-e0a99d0562d248bcbd23e93bf0dc510c
Source dataset
uspto-grants-2012_05
Patent number
US08178543B2

Reaction notes

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