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3-(Bromomethyl)oxolane → 6-Bromo-4-methyl-2-(methylthio)-8-((tetrahydrofuran-3-yl)methyl)pyrido[2,3-d]pyrimidin-7(8H)-one

HRID 641665
Notes
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Reaction equation

HRID 641665 reaction equation
[Br:1][C:2]1[C:14](=[O:15])[NH:13][C:5]2[N:6]=[C:7]([S:11][CH3:12])[N:8]=[C:9]([CH3:10])[C:4]=2[CH:3]=1.Br[CH2:17][CH:18]1[CH2:22][CH2:21][O:20][CH2:19]1>CN(C=O)C>[Br:1][C:2]1[C:14](=[O:15])[N:13]([CH2:17][CH:18]2[CH2:22][CH2:21][O:20][CH2:19]2)[C:5]2[N:6]=[C:7]([S:11][CH3:12])[N:8]=[C:9]([CH3:10])[C:4]=2[CH:3]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 141734223-(Bromomethyl)oxolaneHCID 592589096-bromo-4-methyl-2-(methylthio)pyrido[2,3-d]pyrimidin-7(8H)-one

Product 1

HCID 592589296-Bromo-4-methyl-2-(methylthio)-8-((tetrahydrofuran-3-yl)methyl)pyrido[2,3-d]pyrimidin-7(8H)-oneYield 61.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

To a mixture of 6-bromo-4-methyl-2-(methylthio)pyrido[2,3-d]pyrimidin-7(8H)-one (900 mg, 3.15 mmol) and 3-(bromomethyl)-tetrahydrofuran (571 mg, 3.46 mmol) in DMF was added CsCO3 (1.13 g, 3.46 mmol). After stirred at 70° C. for 7 h and the mixture was quenched with water and extracted with t-butyl ethyl ether (4 times) and concentrated. The crude mixture was purified by flash chromatography, using 0-2% MeOH/CHCl3, to give the title compound (715 mg, 61%).

Workup

  1. customthe mixture was quenched with water
  2. extractionextracted with t-butyl ethyl ether (4 times)
  3. concentrationconcentrated
  4. customThe crude mixture was purified by flash chromatography

Sources & evidence

ORD record
ord-1e6eb24c24e441298ff1062bccdc4a84
Source dataset
uspto-grants-2010_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07696213B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes