Sodium Carbonate → HCID 67050049, compound

HRID 1616101Notes

Reaction equation

HRID 1616101 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.[C:30]([O-])([O-])=[O:31].[Na+].[Na+]>C(O)(=O)C.C=O.CO>[OH:31][CH2:30][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

Participants

6

Reactant 2

HCID 10340Sodium CarbonateHCID 48864908-(2-Methoxyphenyl)-1-methyl-7-phenyl-1H-imidazo[2,1-f]purine-2,4(3H,8H)-dione

Product 1

HCID 67050049HCID 67050049, compoundYield 5%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 712FormaldehydeSolventHCID 887MethanolSolvent

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, 100 mg, 0.258 mmol) in acetic acid (0.387 mL) and formalin (36%, 1.1 mL) was refluxed for 15 h. The solution was then was cooled to room temperature and neutralized with sat. Na2CO3, and the resulting precipitate was filtered off. Cristallization in methanol afforded the desired product as a white solid (6 mg, 5% yield). 1H NMR (500 MHz, DMSO-d6): δ=11.27 (s, 1H), 7.49 (d, J=7.8 Hz, 1H), 7.45 (t, J=7.8 Hz, 1H), 7.32-7.37 (m, 3H), 7.23-7.24 (m, 2H), 7.12 (d, J=7.8 Hz, 1H), 7.05 (t, J=7.8 Hz, 1H), 5.90-5.93 (m, 1H), 4.69-4.72 (m, 2H), 3.55 (s, 3H), 3.32 (s, 3H); 13C NMR (125 MHz, DMSO-d6): δ=154.7, 154.5, 153.6, 150.6, 147.1, 131.1, 129.7, 129.4, 129.2, 128.7, 128.2, 127.0, 122.1, 120.7, 119.4, 112.7, 99.4, 55.5, 52.9, 28.9; IR (film): ν=3134, 2995, 2806, 1668, 1496, 1024, 749, 596 cm−1; HRMS (ESI): m/z: calcd for C22H19N5O4Na+: 440, 1335, found: 440, 1336.

Workup

  1. temperaturewas refluxed for 15 h
  2. filtrationthe resulting precipitate was filtered off

Sources & evidence

ORD record
ord-9163b0a8e92d402297f7b639a5f26b9d
Source dataset
uspto-grants-2014_07
Patent number
US08765775B2

Reaction notes

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