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Sodium Methoxide → 6-(3-methoxypyridin-4-yl)-3-methyl-2-(morpholin-4-yl)-3H-pyrimidin-4-one

HRID 1091397
Notes
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Reaction equation

HRID 1091397 reaction equation
F[C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[C:8]1[N:13]=[C:12]([N:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)[N:11]([CH3:20])[C:10](=[O:21])[CH:9]=1.[CH3:22][O-:23].[Na+]>O1CCCC1>[CH3:22][O:23][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[C:8]1[N:13]=[C:12]([N:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)[N:11]([CH3:20])[C:10](=[O:21])[CH:9]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 578777672-(morpholin-4-yl)-3-methyl-6-(3-fluoropyridin-4-yl)-3H-pyrimidin-4-one

Product 1

HCID 578776546-(3-methoxypyridin-4-yl)-3-methyl-2-(morpholin-4-yl)-3H-pyrimidin-4-oneYield 64%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

A suspension of 6-(3-fluoropyridin-4-yl)-3-methyl-2-(morpholin-4-yl)-3H-pyrimidin-4-one obtained in Example 6-1 (0.60 g, 2.07 mmol), and sodium methoxide (1.37 g, 25.4 mmol) in tetrahydrofuran (15 ml) was heated at 60° C. for 3 hours. The resulting suspension was partitioned between chloroform and brine and the aqueous layer was extracted with chloroform. The combined organic layer was washed with brine, dried over magnesium sulfate, and concentrated in vacuo. The residue was purified by silica gel chromatography eluting 5-10% methanol in chloroform to furnish 6-(3-methoxypyridin-4-yl)-3-methyl-2-(morpholin-4-yl)-3H-pyrimidin-4-one (0.40 g, 1.32 mmol, 64%) as white crystals.

Workup

  1. customThe resulting suspension was partitioned between chloroform and brine
  2. extractionthe aqueous layer was extracted with chloroform
  3. washThe combined organic layer was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel chromatography
  7. washeluting 5-10% methanol in chloroform

Sources & evidence

ORD record
ord-c35ee0b31630463a93f3beb95199385b
Source dataset
uspto-grants-2012_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08129377B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes