Acetic Acid → 2-(dipropylamino)-5-mesityl-7-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-ol

HRID 598131Notes

Reaction equation

HRID 598131 reaction equation
Cl[C:2]1[C:3]2[C:17]([C:18]3[C:23]([CH3:24])=[CH:22][C:21]([CH3:25])=[CH:20][C:19]=3[CH3:26])=[CH:16][N:15]([CH3:27])[C:4]=2[N:5]=[C:6]([N:8]([CH2:12][CH2:13][CH3:14])[CH2:9][CH2:10][CH3:11])[N:7]=1.C(O)(=[O:30])C>[OH-].[Na+].O>[CH2:9]([N:8]([CH2:12][CH2:13][CH3:14])[C:6]1[NH:7][C:2](=[O:30])[C:3]2[C:17]([C:18]3[C:23]([CH3:24])=[CH:22][C:21]([CH3:25])=[CH:20][C:19]=3[CH3:26])=[CH:16][N:15]([CH3:27])[C:4]=2[N:5]=1)[CH2:10][CH3:11]

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 545799764-Chloro-5-mesityl-7-methyl-N,N-dipropyl-7H-pyrrolo[2,3-d]pyrimidin-2-amine

Product 1

HCID 1360006732-(dipropylamino)-5-mesityl-7-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-olYield 81%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 14798Sodium HydroxideSolvent

Procedure

4-Chloro-5-mesityl-7-methyl-N,N-dipropyl-7H-pyrrolo[2,3-d]pyrimidin-2-amine (50 mg, 0.13 mmol) in aqueous sodium hydroxide (2M, 10 ml) was heated at reflux for 6 hours. The solution was cooled to room temperature and neutralized with acetic acid. The mixture was diluted with water (20 ml) and extracted with ethyl acetate (50 ml×3). 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 (4:1) to give 39 mg (81%) of the title compound.

Workup

  1. temperatureat reflux for 6 hours
  2. extractionextracted with ethyl acetate (50 ml×3)
  3. washwashed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel chromatography
  7. washeluting with hexane/ethyl acetate (4:1)

Sources & evidence

ORD record
ord-0a42628fda0a4eb796f2776dcbae9ff5
Source dataset
uspto-grants-2011_03
Patent number
US07897607B2

Reaction notes

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