Sodium ethoxide → HCID 58574723, compound

HRID 1619378Notes

Reaction equation

HRID 1619378 reaction equation
Br[CH2:2][CH2:3][C:4]1[C:9](=[O:10])[N:8]2[CH:11]=[CH:12][C:13]([C:15]#[C:16][C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([F:23])[CH:18]=3)=[CH:14][C:7]2=[N:6][CH:5]=1.CC[O-].[Na+]>CCO.O>[F:23][C:19]1[CH:18]=[C:17]([C:16]#[C:15][C:13]2[CH:12]=[CH:11][N:8]3[C:9](=[O:10])[C:4]([CH:3]=[CH2:2])=[CH:5][N:6]=[C:7]3[CH:14]=2)[CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 2

HCID 2723922Sodium ethoxideHCID 58574126HCID 58574126, compound

Product 1

HCID 58574723HCID 58574723, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of 3-(2-bromoethyl)-8-((3-fluorophenyl)ethynyl)-4H-pyrido[1,2-a]pyrimidin-4-one (289 mg, 0.78 mmol) and EtONa (208 mg, 3.05 mmol) in EtOH (absolute) was stirred at 50° C. for 3 hr. After the suspension was diluted with water (30 mL) and extracted with ethyl acetate (3×50 mL), the combined organic layers were dried over Na2SO4 and concentrated to give the desired product, which was purified by column chromatography. MS (ESI): 291 (MH+); 1H NMR (300 MHz, CDCl3) δ 9.10-9.07 (d, J=7.44 Hz, 1H), 8.44 (s, 1H), 7.76 (s, 1H), 7.42-7.39 (m, 2H), 7.32-7.31 (m, 1H), 7.20-7.17 (m, 2H), 6.86-6.76 (m, 1H), 6.36-6.29 (dd, J=17.65, 1.38 Hz, 1H), 5.50-5.46 (dd, J=11.41, 1.32 Hz, 1H).

Workup

  1. extractionextracted with ethyl acetate (3×50 mL)
  2. dry with materialthe combined organic layers were dried over Na2SO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-7489b6a53bc4437f9b8e0cb196dc3993
Source dataset
uspto-grants-2014_07
Patent number
US08772301B2

Reaction notes

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