Potassium Carbonate → 6-(2-Pyrrolidin-1-yl-ethoxy)-2-pyrrolo[1,2-c]pyrimidin-3-yl-chromen-4-one O-tert-butyl oxime

HRID 1853306Notes

Reaction equation

HRID 1853306 reaction equation
[C:1]([O:5][N:6]=[C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([O:17][CH2:18][CH2:19]Cl)[CH:15]=2)[O:10][C:9]([C:21]2[N:26]=[CH:25][N:24]3[CH:27]=[CH:28][CH:29]=[C:23]3[CH:22]=2)=[CH:8]1)([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[NH:36]1[CH2:40][CH2:39][CH2:38][CH2:37]1>C(#N)C>[C:1]([O:5][N:6]=[C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([O:17][CH2:18][CH2:19][N:36]3[CH2:40][CH2:39][CH2:38][CH2:37]3)[CH:15]=2)[O:10][C:9]([C:21]2[N:26]=[CH:25][N:24]3[CH:27]=[CH:28][CH:29]=[C:23]3[CH:22]=2)=[CH:8]1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 31268PyrrolidineHCID 866730766-(2-chloro-ethoxy)-2-pyrrolo[1,2-c]pyrimidin-3-yl-chromen-4-one O-tert-butyl oxime

Product 1

HCID 866730756-(2-Pyrrolidin-1-yl-ethoxy)-2-pyrrolo[1,2-c]pyrimidin-3-yl-chromen-4-one O-tert-butyl oximeYield 71%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 6-(2-chloro-ethoxy)-2-pyrrolo[1,2-c]pyrimidin-3-yl-chromen-4-one O-tert-butyl oxime (example 87B) (64 mg, 0.16 mmol), potassium carbonate (64 mg, 0.46 mmol) and pyrrolidine (19 μl, 0.24 mmol), in acetonitrile (1.5 ml) was heated in a sealed tube at 100° C. for 18 hours. The yellow suspension was filtered, the solid washed with ethyl acetate and the combined filtrates concentrated to dryness. The residue was purified by silica gel flash chromatography (gradient ethyl acetate/methanol 0-2%) to yield the title compound (49 mg, 71%) as a yellow solid.

Workup

  1. filtrationThe yellow suspension was filtered
  2. washthe solid washed with ethyl acetate
  3. concentrationthe combined filtrates concentrated to dryness
  4. customThe residue was purified by silica gel flash chromatography (gradient ethyl acetate/methanol 0-2%)

Sources & evidence

ORD record
ord-9cd89519f34c43918a49b565ebacd8a8
Source dataset
uspto-grants-2015_02
Patent number
US08962627B2

Reaction notes

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