Sodium Bicarbonate → HCID 58938618, compound

HRID 598190Notes

Reaction equation

HRID 598190 reaction equation
[CH2:1]([N:4]([CH2:34][CH2:35][CH3:36])[C:5]1[N:6]([CH3:33])[C:7](=[O:32])[C:8]2[C:13]([C:14]3[C:19]([CH3:20])=[CH:18][C:17]([CH3:21])=[CH:16][C:15]=3[CH3:22])=[CH:12][N:11](CC3C=CC(OC)=CC=3)[C:9]=2[N:10]=1)[CH2:2][CH3:3].C(=O)([O-])O.[Na+]>FC(F)(F)C(O)=O.C1(OC)C=CC=CC=1.O>[CH2:34]([N:4]([CH2:1][CH2:2][CH3:3])[C:5]1[N:6]([CH3:33])[C:7](=[O:32])[C:8]2[C:13]([C:14]3[C:15]([CH3:22])=[CH:16][C:17]([CH3:21])=[CH:18][C:19]=3[CH3:20])=[CH:12][NH:11][C:9]=2[N:10]=1)[CH2:35][CH3:36]

Participants

6

Reactant 2

HCID 516892Sodium BicarbonateHCID 58938642HCID 58938642, compound

Product 1

HCID 58938618HCID 58938618, compoundYield 15.6%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6422Trifluoroacetic acidSolventHCID 7519AnisoleSolvent

Procedure

A Solution of 2-(dipropylamino)-5-mesityl-7-(4-methoxybenzyl)-3-methyl-3,7-dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-one (100 mg, 0.21 mmol) in trifluoroacetic acid (3 ml) and anisole (0.1 ml) was refluxed for 3 days. The mixture was diluted with water (20 ml), neutralized with sodium hydrogen carbonate and extracted with ethyl acetate (20 ml×2). The extracts were combined, washed with brine, dried over sodium sulfate and concentrated in vacuo. The residue was purified by silica gel chromatography eluting with hexane/ethyl acetate (5:1) to give 12 mg (15%) of the title compound.

Workup

  1. extractionextracted with ethyl acetate (20 ml×2)
  2. washwashed with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by silica gel chromatography
  6. washeluting with hexane/ethyl acetate (5:1)

Sources & evidence

ORD record
ord-8d2351b0c9a941a98b6c0d97405672c0
Source dataset
uspto-grants-2011_03
Patent number
US07897607B2

Reaction notes

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