Methyl iodide → HCID 58574610, compound

HRID 1619385Notes

Reaction equation

HRID 1619385 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]([CH2:18][OH:19])=[CH:16][N:17]=[C:12]3[CH:11]=2)[CH:5]=[CH:6][CH:7]=1.[H-].[Na+].[CH3:25]I>C1COCC1>[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]([CH2:18][O:19][CH3:25])=[CH:16][N:17]=[C:12]3[CH:11]=2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 58574137HCID 58574137, compound

Product 1

HCID 58574610HCID 58574610, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 8-((3-fluorophenyl)ethynyl)-3-(hydroxymethyl)-4H-pyrido[1,2-a]pyrimidin-4-one (16 mg) in anhydrous THF (5 mL) was added NaH (16 mg, 60% in oil) in portions. After the reaction mixture was stirred for 15 min, MeI (0.05 mL) was added. The solution was stirred for 30 min. Then the reaction mixture was quenched with saturated NH4Cl and extracted with ethyl acetate (3×50 mL). The combined organic layers were dried over Na2SO4 and concentrated to give the desired product (11 mg), which was purified by preparative HPLC. MS (ESI): 309 (MH+); 1H NMR (300 MHz, CD3OD) δ 9.07-9.05 (d, J=6.81 Hz, 1H), 8.42 (s, 1H), 7.83 (s, 1H), 7.51-7.48 (m, 2H), 7.44-7.39 (m, 2H), 7.29-7.27 (m, 1H), 4.53 (s, 2H), 3.54-3.50 (d, J=7.02 Hz, 3H). mGluR5 PAM EC50: +++.

Workup

  1. stirringThe solution was stirred for 30 min
  2. customThen the reaction mixture was quenched with saturated NH4Cl
  3. extractionextracted with ethyl acetate (3×50 mL)
  4. dry with materialThe combined organic layers were dried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-d6b56de626af44dda151ea3d7e99b621
Source dataset
uspto-grants-2014_07
Patent number
US08772301B2

Reaction notes

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