Dimethylamine → HCID 59309796, compound

HRID 1513093Notes

Reaction equation

HRID 1513093 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[C:5]([O:10][CH2:11][C:12]2[C:17]([O:18][CH3:19])=[CH:16][CH:15]=[C:14]([F:20])[C:13]=2[F:21])=[CH:4][C:3]=1[N:22]1[C:30](=[O:31])[NH:29][C:28]2[C:23]1=[N:24][C:25]([CH2:34]Cl)=[N:26][C:27]=2[O:32][CH3:33].[CH3:36][NH:37][CH3:38].[I-].[Na+].[Cl-].[NH4+]>CC(O)C.C(#N)C>[Cl:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[C:5]([O:10][CH2:11][C:12]2[C:17]([O:18][CH3:19])=[CH:16][CH:15]=[C:14]([F:20])[C:13]=2[F:21])=[CH:4][C:3]=1[N:22]1[C:30](=[O:31])[NH:29][C:28]2[C:23]1=[N:24][C:25]([CH2:34][N:37]([CH3:38])[CH3:36])=[N:26][C:27]=2[O:32][CH3:33]

Participants

7

Reactant 4

HCID 674DimethylamineHCID 5238Sodium IodideHCID 25517Ammonium ChlorideHCID 68515651HCID 68515651, compound

Product 1

HCID 59309796HCID 59309796, compound

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 9-[2-chloro-5-(2,3-difluoro-6-methoxybenzyloxy)-4-methoxyphenyl]-2-hydroxymethyl-6-methoxy-7,9-dihydro-8H-purin-8-one (0.34 g) and triphenyl-phosphine (0.43 g) in N,N-dimethylformamide (4 mL) was added carbon tetrachloride (1 mL), and the mixture was stirred at room temperature for 2 hours. The reaction mixture was poured into 10% aqueous sodium chloride solution, and the resulting mixture was extracted with ethyl acetate. The extract was washed with brine, and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure, and the residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=1/1−1/20) to give 9-[2-chloro-5-(2,3-difluoro-6-methoxybenzyloxy)-4-methoxyphenyl]-2-chloromethyl-6-methoxy-7,9-dihydro-8H-purin-8-one (0.34 g). The mixture of the obtained 9-[2-chloro-5-(2,3-difluoro-6-methoxybenzyloxy)-4-methoxyphenyl]-2-chloromethyl-6-methoxy-7,9-dihydro-8H-purin-8-one (50 mg), dimethylamine (50% aqueous solution, 0.1 mL) and sodium iodide (14 mg) in 2-propanol (1 mL)-acetonitrile (1 mL) was stirred at 60° C. for 4 hours. The reaction mixture was poured into a saturated aqueous ammonium chloride solution, and the resulting mixture was extracted with ethyl acetate. The extract was washed with brine, and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure, and the residue was purified by column chromatography on silica gel (eluent: ethyl acetate−ethyl acetate/methanol=7/3). The obtained product was suspended in diethyl ether, and collected by filtration. The collected material was dried under reduced pressure to give the title compound (12 mg).

Workup

  1. extractionthe resulting mixture was extracted with ethyl acetate
  2. washThe extract was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was removed under reduced pressure
  5. customthe residue was purified by column chromatography on silica gel (eluent: ethyl acetate−ethyl acetate/methanol=7/3)
  6. filtrationcollected by filtration
  7. customThe collected material was dried under reduced pressure

Sources & evidence

ORD record
ord-19fd9764828043bda1e7e0afab294dbd
Source dataset
uspto-grants-2012_07
Patent number
US08217069B2

Reaction notes

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