N-methyl-2-pyrrolidone → HCID 57597242, compound

HRID 1786945Notes

Reaction equation

HRID 1786945 reaction equation
Cl[C:2]1[C:3]2[N:10]([CH2:11][CH2:12][O:13][CH2:14][CH3:15])[C:9]([C:16]3[O:17][CH:18]=[CH:19][CH:20]=3)=[CH:8][C:4]=2[N:5]=[CH:6][N:7]=1.[CH3:21][C:22]1[CH:23]=[C:24]([CH:26]=[CH:27][C:28]=1[O:29][C:30]1[CH:31]=[N:32][C:33]([CH3:36])=[CH:34][CH:35]=1)[NH2:25].CN1CCCC1=O.C(=O)([O-])O.[Na+]>O>[CH2:14]([O:13][CH2:12][CH2:11][N:10]1[C:3]2[C:2]([NH:25][C:24]3[CH:26]=[CH:27][C:28]([O:29][C:30]4[CH:31]=[N:32][C:33]([CH3:36])=[CH:34][CH:35]=4)=[C:22]([CH3:21])[CH:23]=3)=[N:7][CH:6]=[N:5][C:4]=2[CH:8]=[C:9]1[C:16]1[O:17][CH:18]=[CH:19][CH:20]=1)[CH3:15]

Participants

6

Reactant 4

HCID 13387N-methyl-2-pyrrolidoneHCID 516892Sodium BicarbonateHCID 114244343-Methyl-4-((6-methylpyridin-3-yl)oxy)anilineHCID 860847954-Chloro-5-(2-ethoxyethyl)-6-(2-furanyl)-5H-pyrrolo[3,2-d]pyrimidine

Product 1

HCID 57597242HCID 57597242, compoundYield 63.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 4-chloro-5-(2-ethoxyethyl)-6-(2-furyl)-5H-pyrrolo[3,2-d]pyrimidine (76 mg), 3-methyl-4-[(6-methylpyridin-3-yl)oxy]aniline (67 mg) and 1-methyl-2-pyrrolidinone (1.5 mL) was stirred at 140° C. for 2 hrs, poured into water (8 mL) and adjusted to pH 8 with saturated aqueous sodium hydrogen carbonate. The mixture was extracted with ethyl acetate (20 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. Diisopropyl ether-hexane 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 (78 mg).

Workup

  1. extractionThe mixture was extracted with ethyl acetate (20 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. additionDiisopropyl ether-hexane 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-da144fcb7f254543bff93793120ab243
Source dataset
uspto-grants-2009_03
Patent number
US07507740B2

Reaction notes

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