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Potassium Hydroxide → 4-((2-Ethyl-5,7-dimethylpyrazolo[1,5-a]pyrimidin-3-yl)methyl)phenol

HRID 403485
Notes
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Reaction equation

HRID 403485 reaction equation
[OH-:1].[K+].Br[C:4]1[CH:23]=[CH:22][C:7]([CH2:8][C:9]2[C:10]([CH2:20][CH3:21])=[N:11][N:12]3[C:17]([CH3:18])=[CH:16][C:15]([CH3:19])=[N:14][C:13]=23)=[CH:6][CH:5]=1>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH2:20]([C:10]1[C:9]([CH2:8][C:7]2[CH:22]=[CH:23][C:4]([OH:1])=[CH:5][CH:6]=2)=[C:13]2[N:14]=[C:15]([CH3:19])[CH:16]=[C:17]([CH3:18])[N:12]2[N:11]=1)[CH3:21]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 683789033-(4-Bromobenzyl)-2-ethyl-5,7-dimethylpyrazolo[1,5-A]pyrimidine

Product 1

HCID 683792244-((2-Ethyl-5,7-dimethylpyrazolo[1,5-a]pyrimidin-3-yl)methyl)phenol

Reagents, catalysts & solvents 1

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst

Conditions

Temperature
100 °C

Procedure

Potassiumhydroxide (1.96 g, 34.9 mmol) was dissolved in 30 ml of a 1:1 mixture of argon-flushed dioxane and water. After addition of 3-(4-bromo-benzyl)-2-ethyl-5,7-dimethyl-pyrazolo[1,5-a]pyrimidine (3) (4 g, 11.62 mmol), Pd2(dba)3 (426 mg, 0.465 mmol) and tetramethyl Xphos (894 mg, 1.859 mmol), the mixture was flushed with argon and stirred for 1 h at 100° C. Then the mixture was treated with 1N HCl and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over Na2 SO4 and evaporated. Purification by chromatography (silica gel, ethylaceta/n-heptane) gave a yellow solid.

Workup

  1. customflushed dioxane and water
  2. customthe mixture was flushed with argon
  3. additionThen the mixture was treated with 1N HCl
  4. extractionextracted with ethyl acetate
  5. washThe combined organic layers were washed with brine
  6. customdried over Na2 SO4
  7. customevaporated
  8. customPurification by chromatography (silica gel, ethylaceta/n-heptane)
  9. customgave a yellow solid

Sources & evidence

ORD record
ord-878f69bebbad48dba2d8c12d0f021e7d
Source dataset
uspto-grants-2014_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08748435B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes