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Sodium Methoxide → 4-Methoxy-6-(2-phenylethynyl)-5-pyrimidin-5-ylpyridin-2-amine

HRID 535390
Notes
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Reaction equation

HRID 535390 reaction equation
Cl[C:2]1[C:7]([C:8]2[CH:9]=[N:10][CH:11]=[N:12][CH:13]=2)=[C:6]([C:14]#[C:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[N:5]=[C:4]([NH2:22])[CH:3]=1.[CH3:23][O-:24].[Na+]>CO.O>[CH3:23][O:24][C:2]1[C:7]([C:8]2[CH:9]=[N:10][CH:11]=[N:12][CH:13]=2)=[C:6]([C:14]#[C:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[N:5]=[C:4]([NH2:22])[CH:3]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 10942334Sodium MethoxideHCID 866943744-Chloro-6-(2-phenylethynyl)-5-pyrimidin-5-ylpyridin-2-amine

Product 1

HCID 866943754-Methoxy-6-(2-phenylethynyl)-5-pyrimidin-5-ylpyridin-2-amine

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 4-chloro-6-(2-phenylethynyl)-5-pyrimidin-5-ylpyridin-2-amine C3c (400 mg, 1.3 mmol), sodium methoxide (a solution of 2.61 mmol in 0.29 ml MeOH) and MeOH (2 ml) is stirred for 20 minutes at 100° C. and 10 minutes at 110° C. The mixture is diluted with water and extracted with DCM. The combined organic layers are dried over Na2SO4, concentrated in vacuo and the product purified by NP chromatography. Yield: 228 mg (58%). HPLC-MS: M+H=303.

Workup

  1. extractionextracted with DCM
  2. dry with materialThe combined organic layers are dried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. customthe product purified by NP chromatography

Sources & evidence

ORD record
ord-bcfa975a25bb4444b244572464c091b6
Source dataset
uspto-grants-2014_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08859541B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes