1,4-Dioxane → HCID 86637289, compound

HRID 1876859Notes

Reaction equation

[Cl:1][C:2]1[N:7]=[C:6](Cl)[C:5]([CH3:9])=[CH:4][N:3]=1.[CH:10]1([CH:15]([N:19]2[CH:23]=[C:22](B3OC(C)(C)C(C)(C)O3)[CH:21]=[N:20]2)[CH2:16][C:17]#[N:18])[CH2:14][CH2:13][CH2:12][CH2:11]1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].O1CCOC[CH2:42]1>O.CCOC(C)=O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:1][C:2]1[N:7]=[C:6]([C:22]2[CH:21]=[N:20][N:19]([CH:15]([CH:10]3[CH2:14][CH2:13][CH2:12][CH2:11]3)[CH2:16][C:17]#[N:18])[CH:23]=2)[C:5]([CH2:9][CH3:42])=[CH:4][N:3]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 2,4-dichloro-5-methylpyrimidine (0.62 g, 3.8 mmol), 3-cyclopentyl-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)propanenitrile (1.0 g, 3.17 mmol), tetrakis(triphenylphosphine)palladium (200 mg, 0.2 mmol), and potassium phosphate (2.0 g, 9.6 mmol) in 1,4-dioxane (9 mL) and water (0.9 mL) was heated at 100° C. overnight. After cooling to room temperature, the mixture was diluted with EtOAc, washed with water, brine, dried over MgSO4, concentrated. The residue was purified on silica gel, eluting with 0 to 80% EtOAc-hexanes, to give the desired product (780 mg, 78%). LCMS (M+H) 316.0.

Workup

temperatureAfter cooling to room temperature
washwashed with water, brine
dry with materialdried over MgSO4
concentrationconcentrated
customThe residue was purified on silica gel
washeluting with 0 to 80% EtOAc-hexanes

Sources & evidence

ORD record: ord-772610f42eec48f781d592eb9f011dac
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08309718B2

Reaction notes

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