Ethanol → HCID 58902026, compound

HRID 1992415Notes

Reaction equation

HRID 1992415 reaction equation
[Cl:1][C:2]1[C:3]2[N:4]([C:8](=[O:27])[NH:9][C:10]=2[C:11]2[CH:20]=[C:19]3[C:14]([CH:15]=[CH:16][C:17]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)=[N:18]3)=[CH:13][CH:12]=2)[CH:5]=[CH:6][N:7]=1.[CH2:28](O)[CH3:29].CN1CCCN(C)C1=O.ICC>C(=O)([O-])[O-].[Ag+2]>[Cl:1][C:2]1[C:3]2[N:4]([C:8]([O:27][CH2:28][CH3:29])=[N:9][C:10]=2[C:11]2[CH:20]=[C:19]3[C:14]([CH:15]=[CH:16][C:17]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)=[N:18]3)=[CH:13][CH:12]=2)[CH:5]=[CH:6][N:7]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 6340IodoethaneHCID 816462(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl-HCID 136038646HCID 136038646, compound

Product 1

HCID 58902026HCID 58902026, compound

Reagents, catalysts & solvents 1

HCID 178418647HCID 178418647, compoundCatalyst

Conditions

Temperature
40 °C

Procedure

A 80 mL sealed tube is charged with 8-chloro-1-(2-phenyl-quinolin-7-yl)-2H-imidazo[1,5-a]pyrazin-3-one (50.00 mg, 0.1341 mmol), silver carbonate (74 mg, 0.27 mmol), anhydrous ethanol (2.00 mL, 0.034 mol), 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (0.002 mL, 0.01 mmol), and iodoethane (0.012 mL, 0.15 mmol). The reaction was sealed under an atmosphere of nitrogen and heated at 40° C. for 24 hours. The reaction was cooled and filtered. Water and EtOAc were added and the organic layer was isolated, dried over sodium sulfate, filtered and concentrated in vacuo to yield a yellow gum. The crude product was purified via silica gel column chromatography, (Jones, 5 gram column eluting with 50% EtOAc: Hex) to yield the title compound as a yellow gum; MS (ES+): m/z 401.03 (100) [MH+], 402.98 (30) [MH+++]; HPLC: tR=4.13 min (OpenLynx, polar—5 min); 1HNMR (400 MHz, CHLOROFORM-d) δ ppm 1.41-1.72 (m, 3H), 4.55-4.86 (m, 2H), 7.18 (d, J=4.80 Hz, 1H), 7.38-7.65 (m, 4H), 7.75-8.00 (m, 3H), 8.09-8.33 (m, 3H), 8.52 (br. s., 1H).

Workup

  1. customA 80 mL sealed tube
  2. customThe reaction was sealed under an atmosphere of nitrogen
  3. temperatureThe reaction was cooled
  4. filtrationfiltered
  5. additionWater and EtOAc were added
  6. customthe organic layer was isolated
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customto yield a yellow gum
  11. customThe crude product was purified via silica gel column chromatography, (Jones, 5 gram column eluting with 50% EtOAc: Hex)

Sources & evidence

ORD record
ord-e1aaf2b07e37406f8d9d50a9eeacb87a
Source dataset
uspto-grants-2010_01
Patent number
US07648987B2

Reaction notes

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