Ethanol → HCID 58574406, compound

HRID 1619377Notes

Reaction equation

HRID 1619377 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:8]#[C:9][C:10]2[CH:22]=[CH:21][N:13]3[C:14](=[O:20])[C:15]([CH:18]=[CH2:19])=[CH:16][N:17]=[C:12]3[CH:11]=2)[CH:5]=[CH:6][CH:7]=1.C([OH:25])C>>[F:1][C:2]1[CH:3]=[C:4]([C:8]#[C:9][C:10]2[CH:22]=[CH:21][N:13]3[C:14](=[O:20])[C:15]([CH:18]([OH:25])[CH3:19])=[CH:16][N:17]=[C:12]3[CH:11]=2)[CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 702EthanolHCID 58574723HCID 58574723, compound

Product 1

HCID 58574406HCID 58574406, compound

Procedure

8-((3-fluorophenyl)ethynyl)-3-vinyl-4H-pyrido[1,2-a]pyrimidin-4-one (30 mg, 0.1 mmol) was added into a saturated HO/ethanol (5 mL) solution. After stirring at ambient temperature for 3 h, the solution was adjusted to pH=8 and extracted with ethyl acetate (3×50 mL). The combined organic layers were dried over Na2SO4 and concentrated to give the crude product, which was purified by column chromatography. MS (ESI): 309 (MH+); 1H NMR (300 MHz, CDCl3) δ 9.01-8.99 (d, J=7.44 Hz, 1H), 8.38 (s, 1H), 7.77 (s, 1H), 7.45-7.39 (m, 2H), 7.33-7.28 (m, 1H), 7.20 (m, 1H), 7.17 (m, 1H), 5.11-5.02 (m, 1H), 3.54-3.52 (d, J=6.03 Hz, 1H), 2.62-2.57 (d, J=6.6 Hz, 3H). mGluR5 PAM EC50: ++. Fold shift at 10 μM: +.

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-597ac12ba99640ad850dbe8b881b4936
Source dataset
uspto-grants-2014_07
Patent number
US08772301B2

Reaction notes

Loading…