Water → HCID 86637302, compound

HRID 1876892Notes

Reaction equation

HRID 1876892 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[CH:5]=[CH:4][N:3]=1.[O:9]1[CH2:14][CH2:13][CH:12]([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])[CH2:11][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:22]2[CH:21]=[N:20][N:19]([CH:15]([CH:12]3[CH2:13][CH2:14][O:9][CH2:10][CH2:11]3)[CH2:16][C:17]#[N:18])[CH:23]=2)[CH:5]=[CH:4][N:3]=1

Participants

8

Reactant 5

HCID 962WaterHCID 312751,4-DioxaneHCID 62657Potassium Phosphate, TribasicHCID 775312,4-DichloropyrimidineHCID 68756140HCID 68756140, compound

Product 1

HCID 86637302HCID 86637302, compoundYield 71.4%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2,4-dichloropyrimidine (0.589 g, 0.00395 mol), 3-(tetrahydro-2H-pyran-4-yl)-3-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]propanenitrile (1.30 g, 0.00392 mol), tetrakis(triphenylphosphine)palladium(0) (0.3 g, 0.0002 mol), and potassium phosphate (2.5 g, 0.012 mol) in 1,4-dioxane (10 mL, 0.1 mol) and water (1 mL, 0.06 mol) was heated at 100° C. overnight. After cooling to room temperature, the mixture was diluted with EtOAc, washed with water, brine, dried over MgSO4, filtered and concentrated. The residue was purified on silica gel, eluting with 0 to 100% EtOAc in hexanes, to provide the desired product (890 mg, 71.36%). LCMS (M+H) 318.3

Workup

  1. temperatureAfter cooling to room temperature
  2. washwashed with water, brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified on silica gel
  7. washeluting with 0 to 100% EtOAc in hexanes

Sources & evidence

ORD record
ord-5409d7bdf40744ed860e274d2bacd81c
Source dataset
uspto-grants-2012_11
Patent number
US08309718B2

Reaction notes

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