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

HRID 403485Notes

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]

Participants

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

customflushed dioxane and water
customthe mixture was flushed with argon
additionThen the mixture was treated with 1N HCl
extractionextracted with ethyl acetate
washThe combined organic layers were washed with brine
customdried over Na2 SO4
customevaporated
customPurification by chromatography (silica gel, ethylaceta/n-heptane)
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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