Potassium Phosphate, Tribasic → HCID 86637292, compound

HRID 1876868Notes

Reaction equation

[Cl:1][C:2]1[N:7]=[C:6](Cl)[CH:5]=[CH:4][N:3]=1.[CH:9]1([CH:13]([N:17]2[CH:21]=[C:20](B3OC(C)(C)C(C)(C)O3)[CH:19]=[N:18]2)[CH2:14][C:15]#[N:16])[CH2:12][CH2:11][CH2:10]1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.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:20]2[CH:19]=[N:18][N:17]([CH:13]([CH:9]3[CH2:12][CH2:11][CH2:10]3)[CH2:14][C:15]#[N:16])[CH:21]=2)[CH:5]=[CH:4][N:3]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 2,4-dichloropyrimidine (4.8 g, 0.032 mol), 3-cyclobutyl-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)propanenitrile (8.10 g, 0.0269 mol), tetrakis(triphenylphosphine)palladium (2.0 g, 0.002 mol), and potassium phosphate (17 g, 0.081 mol) in 1,4-dioxane (80 mL) and water (8 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, and concentrated. The residue was purified on silica gel, eluting with 0 to 80%, to give the desired product (5.51 g, 71.2%). LCMS (M+H) 288.3.

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%

Sources & evidence

ORD record: ord-7431e726d1a4463bace4cf89f138ec8d
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08309718B2

Reaction notes

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