Tetrahydrofuran → HCID 86658260, compound

HRID 1040206Notes

Reaction equation

HRID 1040206 reaction equation
[CH3:1][C:2]([OH:19])([CH3:18])[CH2:3][N:4]1[CH:8]=[C:7](B2OC(C)(C)C(C)(C)O2)[CH:6]=[N:5]1.[Cl:20][C:21]1[N:26]=[C:25](Cl)[CH:24]=[CH:23][N:22]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].C1COCC1>O>[Cl:20][C:21]1[N:26]=[C:25]([C:7]2[CH:6]=[N:5][N:4]([CH2:3][C:2]([CH3:1])([OH:19])[CH3:18])[CH:8]=2)[CH:24]=[CH:23][N:22]=1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 62657Potassium Phosphate, TribasicHCID 775312,4-DichloropyrimidineHCID 582041312-methyl-1-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]propan-2-ol

Product 1

HCID 86658260HCID 86658260, compoundYield 58.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

To a mixture of the product from Step 1 (84 mg, 0.31 mmol), 2,4-dichloropyrimidine (47 mg, 0.31 mmol), potassium phosphate, tribasic (167 mg, 0.79 mmol), and 1,1′-bis(diphenylphosphino)ferrocene-palladium(II)-dichloride dichloromethane complex (26 mg, 0.031 mmol) was added THF (2 mL) and water (0.2 mL). The mixture was heated to 120° C. for 15 minutes under microwave irradiation, cooled to room temperature, quenched with 1:1 water:brine, and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, filtered, and concentrated. Purification by column chromatography on silica gel (Biotage 10 G, eluting with 0:100 to 100:0 ethyl acetate:hexanes) afforded 1-[4-(2-chloropyrimidin-4-yl)-1H-pyrazol-1-yl]-2-methylpropan-2-ol (44 mg, 0.18 mmol, 56% yield) as a yellow solid. MS ESI: [M+H]+ m/z 253.0.

Workup

  1. temperaturecooled to room temperature
  2. customquenched with 1:1 water
  3. extractionbrine, and extracted with ethyl acetate
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by column chromatography on silica gel (Biotage 10 G, eluting with 0:100 to 100:0 ethyl acetate:hexanes)

Sources & evidence

ORD record
ord-e95db509d7e5495794dc919c33cafc79
Source dataset
uspto-grants-2013_10
Patent number
US08551984B2

Reaction notes

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