Sodium Carbonate → HCID 86758703, compound

HRID 2298881Notes

Reaction equation

HRID 2298881 reaction equation
Cl.[CH2:2]1[C:7]2[O:8][C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[C:6]=2[CH2:5][CH2:4][NH:3]1.Cl[CH2:16][CH2:17][C:18]1[C:23](=[O:24])[N:22]2[CH:25]=[CH:26][CH:27]=[CH:28][C:21]2=[N:20][C:19]=1[CH3:29].[C:30]([O-:33])([O-:32])=O.[Na+].[Na+]>CC(=O)CC>[C:7]([OH:24])(=[O:8])/[CH:6]=[CH:10]/[C:30]([OH:33])=[O:32].[CH2:2]1[C:7]2[O:8][C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[C:6]=2[CH2:5][CH2:4][N:3]1[CH2:16][CH2:17][C:18]1[C:23](=[O:24])[N:22]2[CH:25]=[CH:26][CH:27]=[CH:28][C:21]2=[N:20][C:19]=1[CH3:29]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 8178663-(2-Chloroethyl)-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-oneHCID 139252361,2,3,4-Tetrahydrobenzofuro[2,3-c]pyridine hydrochloride

Product 1

HCID 86758703HCID 86758703, compoundYield 120.2%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture of 1,2,3,4-tetrahydro-benzofuro[2,3-c]pyridine hydrochloride (1:1) (0.007 mol), 3-(2-chloroethyl)-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one(0.012 mol), Na2CO3 (0.015 mol) and KI (catalytic quantity) in 2-butanone (100 ml) was stirred and refluxed overnight. The reaction mixture was filtered hot and the filtrate was evaporated. The residue was purified by column chromatography over silica gel (eluent: CH2Cl2/(CH3OH/NH3) from 98/2 to 97/3). The purest fractions were collected and the solvent was evaporated. The residue was dissolved in 2-propanol and (E)-2-butenedioic acid (1 g) was added. The mixture was boiled and then stirred at RT. The precipitate was filtered off and dried, yielding 2.00 g (61%) of 3-[2-(3,4-dihydro-benzofuro[2,3-c]pyridin-2(1H)-yl)ethyl]-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one (E)-2-butenedioate (2:1) (compound 1).

Workup

  1. temperaturerefluxed overnight
  2. filtrationThe reaction mixture was filtered hot
  3. customthe filtrate was evaporated
  4. customThe residue was purified by column chromatography over silica gel (eluent: CH2Cl2/(CH3OH/NH3) from 98/2 to 97/3)
  5. customThe purest fractions were collected
  6. customthe solvent was evaporated
  7. dissolutionThe residue was dissolved in 2-propanol
  8. addition(E)-2-butenedioic acid (1 g) was added
  9. stirringstirred at RT
  10. filtrationThe precipitate was filtered off
  11. customdried

Sources & evidence

ORD record
ord-96802ef4f696499da5051b782b8d9be4
Source dataset
uspto-grants-2002_12
Patent number
US06495555B1

Reaction notes

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