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Dimethylformamide → 5-Mesityl-2-[(2-methoxyethyl)amino]-3,7-dimethyl-3,7-dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-one

HRID 598122
Notes
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Reaction equation

HRID 598122 reaction equation
[NH2:1][C:2]1[N:3]([CH3:22])[C:4](=[O:21])[C:5]2[C:10]([C:11]3[C:16]([CH3:17])=[CH:15][C:14]([CH3:18])=[CH:13][C:12]=3[CH3:19])=[CH:9][N:8]([CH3:20])[C:6]=2[N:7]=1.CN(C)C=O.[H-].[Na+].[CH3:30][O:31][CH2:32][CH2:33]Br>O>[C:12]1([CH3:19])[CH:13]=[C:14]([CH3:18])[CH:15]=[C:16]([CH3:17])[C:11]=1[C:10]1[C:5]2[C:4](=[O:21])[N:3]([CH3:22])[C:2]([NH:1][CH2:33][CH2:32][O:31][CH3:30])=[N:7][C:6]=2[N:8]([CH3:20])[CH:9]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6228Dimethylformamide2×HCID 24758Sodium hydrideHCID 809722-Bromoethyl methyl etherHCID 672673282-Amino-5-mesityl-3,7-dimethyl-3,7-dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-one

Product 1

HCID 589386195-Mesityl-2-[(2-methoxyethyl)amino]-3,7-dimethyl-3,7-dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-oneYield 23.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 2-amino-5-mesityl-3,7-dimethyl-3,7-dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-one (55 mg, 0.18 mmol) and N,N-dimethylformamide (2 ml) was added sodium hydride (60% in oil, 24 mg, 0.60 mmol) at 0° C. and stirred for 0.5 hour. After stirring at room temperature for 0.5 hour, to the mixture was added a solution of 2-methoxyethylbromide (232 mg, 0.60 mmol) and N,N-dimethylformamide (1 ml) at 0° C. and stirred for 0.5 hour. After stirring at room temperature for 2 hours and heating under reflux for 2 hours, the mixture was diluted with water (20 ml) and extracted with ethyl acetate (50 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 (9:1) to give 15 mg (23%) of the title compound as an oil.

Workup

  1. stirringAfter stirring at room temperature for 0.5 hour, to the mixture
  2. stirringstirred for 0.5 hour
  3. stirringAfter stirring at room temperature for 2 hours
  4. temperatureheating
  5. temperatureunder reflux for 2 hours
  6. extractionextracted with ethyl acetate (50 ml×2)
  7. washwashed with brine
  8. dry with materialdried over sodium sulfate
  9. concentrationconcentrated in vacuo
  10. customThe residue was purified by silica gel chromatography
  11. washeluting with hexane/ethyl acetate (9:1)

Sources & evidence

ORD record
ord-8fd1316664134612a5439380c05dce0d
Source dataset
uspto-grants-2011_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07897607B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes