Water → HCID 58212086, compound

HRID 1616102Notes

Reaction equation

HRID 1616102 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[C:13]2=[N:14][C:15]3[N:16]([CH3:23])[C:17](=[O:22])[NH:18][C:19](=[O:21])[C:20]=3[N:12]2[CH:11]=[C:10]1[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.O.[CH3:31][CH2:32][O:33]C(C)=O>OS(O)(=O)=O.C(OC(=O)C)(=O)C>[C:32]([C:11]1[N:12]2[C:13](=[N:14][C:15]3[N:16]([CH3:23])[C:17](=[O:22])[NH:18][C:19](=[O:21])[C:20]=32)[N:9]([C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=2[O:2][CH3:1])[C:10]=1[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)(=[O:33])[CH3:31]

Participants

6

Reactant 3

HCID 962WaterHCID 8857Ethyl AcetateHCID 48864908-(2-Methoxyphenyl)-1-methyl-7-phenyl-1H-imidazo[2,1-f]purine-2,4(3H,8H)-dione

Product 1

HCID 58212086HCID 58212086, compoundYield 39%

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidSolventHCID 7918Acetic AnhydrideSolvent

Procedure

A mixture of commercially available 8-(2-methoxyphenyl)-1-methyl-7-phenyl-1H-imidazo[2,1-f]purine-2,4(3H,8H)-dione (5, 200 mg, 0.516 mmol) in concentrated H2SO4 (0.103 mL) and acetic anhydride (1.29 mL) was refluxed for 2 h. The reaction was cooled to room temperature, poured into 10 mL of water, and extracted with CH2Cl2 (2×10 mL). The organic extracts were dried over MgSO4 and evaporated under reduced pressure. Purification by column chromatography on silica gel using a gradient CH2Cl2:EtOAc from 5:1 to 1:1 afforded the desired compound as a white solid (88 mg, 39% yield). 1H NMR (500 MHz, DMSO-d6): δ=11.03 (s, 1H), 7.54 (d, J=7.9 Hz, 1H), 7.42 (t, J=7.8 Hz, 1H), 7.30-7.37 (m, 5H), 7.08 (d, J=7.9 Hz, 1H), 7.02 (t, J=7.8 Hz, 1H), 3.60 (s, 3H), 3.30 (s, 3H), 2.46 (s, 3H); 13C NMR (100 MHz, DMSO-d6, CDCl3): δ=187.6, 154.4, 153.6, 153.0, 150.6, 146.8, 135.7, 131.4, 130.7, 129.8, 129.6, 127.5, 126.4, 121.2, 120.6, 120.1, 112.5, 101.0, 55.5, 29.6, 28.8; IR (film): ν=3160, 3050, 1668, 1490, 1292, 1211, 1023, 751, 555 cm−1; HRMS (ESI): m/z: calcd for C23H19N5O4Na+: 452.1335, found: 452.1338.

Workup

  1. temperaturewas refluxed for 2 h
  2. extractionextracted with CH2Cl2 (2×10 mL)
  3. dry with materialThe organic extracts were dried over MgSO4
  4. customevaporated under reduced pressure
  5. customPurification by column chromatography on silica gel using a gradient CH2Cl2

Sources & evidence

ORD record
ord-5260923fdaaa4c72bc5d2873abc0a999
Source dataset
uspto-grants-2014_07
Patent number
US08765775B2

Reaction notes

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