Potassium Carbonate → HCID 21220556, compound

HRID 2377247Notes

Reaction equation

HRID 2377247 reaction equation
Cl[C:2]1[N:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[OH:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[C:14](=[O:18])[CH2:13][CH2:12]2.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[N:3]1[CH:4]=[CH:5][CH:6]=[N:7][C:2]=1[O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[C:14](=[O:18])[CH2:13][CH2:12]2

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 744042-ChloropyrimidineHCID 2331475-Hydroxy-1-indanone

Product 1

HCID 21220556HCID 21220556, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2-chloropyrimidine (220 mg, 1.9 mmol), 5-hydroxyindan-1-one (209 mg, 1.4 mmol) and potassium carbonate (250 mg, 1.8 mmol) in N,N-dimethyl formamide (5 mL) was heated to about 100° C. overnight. The reaction was cooled to room temperature and the solvent was evaporated under high vacuum. The residue was purified by flash column chromatography on silica gel using ethyl acetate/methanol (99:1) as the mobile phase to provide the desired product. 1H NMR (500 MHz, CDCl3): δ 2.75 (t, J=7 Hz, 2H), 3.18 (t, J=7 Hz, 2H), 7.09 (m, 1H), 7.25 (d, J=7 Hz, 1H), 7.32 (s, 1H), 7.82 (d, J=7 Hz, 1H), 8.62 (d, J=7 Hz, 1H).

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. customthe solvent was evaporated under high vacuum
  3. customThe residue was purified by flash column chromatography on silica gel

Sources & evidence

ORD record
ord-ed5011ee58f74f269e0ed2d25cde1417
Source dataset
uspto-grants-2008_12
Patent number
US07468371B2

Reaction notes

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