Hydrochloric Acid → HCID 9803112, compound

HRID 986947Notes

Reaction equation

HRID 986947 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:10]([CH3:21])[C:11]([CH3:20])=[C:12]2[C:17](=O)[NH:16][C:15]([CH3:19])=[N:14][C:13]=12.[C:22](#[N:24])[CH3:23].Cl.C(Cl)Cl.[CH3:29][OH:30].[O:31]1[CH2:36]CO[CH2:33][CH2:32]1>>[CH3:29][O:30][CH2:23][CH2:22][N:24]([CH2:33][CH2:32][O:31][CH3:36])[C:17]1[C:12]2[C:13](=[C:9]([C:3]3[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=3[Cl:1])[N:10]([CH3:21])[C:11]=2[CH3:20])[N:14]=[C:15]([CH3:19])[N:16]=1

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 6342AcetonitrileHCID 312751,4-DioxaneHCID 21226129Dichloromethane methanolHCID 135744200HCID 135744200, compound

Product 1

HCID 9803112HCID 9803112, compound

Procedure

Part E: 7-(2,4-Dichlorophenyl)-2,5,6-trimethyl-pyrrolo[3,4-d]pyrimidine-4(3H)-one: The compound of part D of Example 1 (0.25 g, 0.764 mmol) was dissolved in dioxane (2.0 mL) and acetonitrile (2.0 mL) and cooled to 15° C. under nitrogen. Dry HCl (gas) was passed through a syringe needle into the reaction mixture over a period of 4 h. TLC(eluent: 10:1 CH2Cl2/methanol) revealed presence of two new spots at Rf=0.27 and 0.46 (faint) along with unreacted starting material spot at Rf=0.80. Stopped bubbling HCl gas at this stage and allowed to stir at room temp. over night. TLC (eluent: 10:1 CH2Cl2/methanol) revealed absence of starting material spot and also the faint spot at Rf=0.46. The only spot noticed was at Rf=0.27 and mass spectrum revealed formation of acetonitrile addition product (M+H=368). The solvent was removed under vacuum, residue was dissolved in 4.0 mL of 1:1 EtOH/water and basified using 28% ammonium hydroxide to pH 9 to 10. Some solid separation was noticed, but extraction of the mixture with ethyl acetate (15 mL) resulted in separation of white solid. Filtered the solid, washed with ethyl acetate, and dried to afford (0.159 g) desired product. Additional 60 mg of product was obtained by extraction of the aq. layer with EtOAc. Overall yield 0.22 g (88% yield, mp>290° C.). Anal. calcd. for C15H13Cl2N3O: C, 55.92; H, 4.089; N,13.04. Found: C, 55.77; H, 3.99; N, 12.80.

Workup

  1. customStopped bubbling HCl gas at this stage
  2. additionformation of acetonitrile addition product (M+H=368)
  3. customThe solvent was removed under vacuum, residue
  4. dissolutionwas dissolved in 4.0 mL of 1:1 EtOH/water
  5. customSome solid separation
  6. extractionextraction of the mixture with ethyl acetate (15 mL)
  7. customresulted in separation of white solid
  8. filtrationFiltered the solid
  9. washwashed with ethyl acetate
  10. customdried

Sources & evidence

ORD record
ord-af1a44312a4b4c4f9da06f892646afcb
Source dataset
uspto-grants-2003_10
Patent number
US06630476B2

Reaction notes

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