Sodium hydride → Methyl 2-(1-methyl-6-oxopyrido[2,3-e]pyrrolo[1,2-a]pyrazin-5(6H)-yl)acetate

HRID 526042

Reaction equation

HRID 526042 reaction equation
[CH3:1][C:2]1[C:11]2[N:10]3[CH:12]=[CH:13][CH:14]=[C:9]3[C:8](=[O:15])[NH:7][C:6]=2[N:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH3:18][O:19][C:20](=[O:23])[CH2:21]Br>CN(C=O)C>[CH3:1][C:2]1[C:11]2[N:10]3[CH:12]=[CH:13][CH:14]=[C:9]3[C:8](=[O:15])[N:7]([CH2:21][C:20]([O:19][CH3:18])=[O:23])[C:6]=2[N:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 60984Methyl bromoacetateHCID 894450501-Methylpyrido[2,3-e]pyrrolo[1,2-a]pyrazin-6(5H)-one

Product 1

HCID 89451658Methyl 2-(1-methyl-6-oxopyrido[2,3-e]pyrrolo[1,2-a]pyrazin-5(6H)-yl)acetate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-methylpyrido[2,3-e]pyrrolo[1,2-a]pyrazin-6(5H)-one (50 mg, 0.25 mmol) in 2 mL of DMF, was added NaH (60%, 11 mg, 0.28 mmol). The mixture was stirred at room temperature for 1 hour. Methylbromoacetate (26 mL, 0.28 mmol) was added. The mixture was stirred for 16 hours. Solvents were removed under vacuum and the residue was purified by silica gel flash chromatography. (DCM/MeOH=1:10, Rf=0.5) to afford 37 mg (54%) light yellow solid. 1H NMR (400 MHz, CDCl3) δ 8.15 (d, J=4.9 Hz, 1H), 7.95 (dd, J=1.5, 2.9 Hz, 1H) 7.36 (dd, J=1.5, 4.0 Hz, 1H), 7.00 (d, J=4.9 Hz, 1H), 6.71 (dd, J=2.9, 4.0 Hz, 1H), 5.25 (s, 2H), 3.77 (s, 3H), 2.83 (s, 3H). 13C NMR (101 MHz, CDCl3) δ 169.3, 155.5, 143.1, 142.1, 134.8, 124.2, 122.7, 122.6, 120.4, 113.5, 113.4, 52.3, 41.9, 22.9. HRMS (m/z): calcd for C14H34N3O3 (M+H) 272.1035. found 272.1042.

Workup

  1. stirringThe mixture was stirred for 16 hours
  2. customSolvents were removed under vacuum
  3. customthe residue was purified by silica gel flash chromatography
  4. custom(DCM/MeOH=1:10, Rf=0.5) to afford 37 mg (54%) light yellow solid

Sources & evidence

ORD record
ord-422c20fc69b2451eaa5c13627344e1c4
Source dataset
uspto-grants-2016_05
Patent number
US09345703B2

Linked notes

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