Water → 2-(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyrimidine

HRID 468643Notes

Reaction equation

HRID 468643 reaction equation
Br[C:2]1[N:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[C:8]1(B2OC(C)(C)C(C)(C)O2)[CH:13]=[CH:12][C:11]([B:14]2[O:18][C:17]([CH3:20])([CH3:19])[C:16]([CH3:22])([CH3:21])[O:15]2)=[CH:10][CH:9]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].O>CN(C=O)C.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>[CH3:19][C:17]1([CH3:20])[C:16]([CH3:21])([CH3:22])[O:15][B:14]([C:11]2[CH:12]=[CH:13][C:8]([C:2]3[N:7]=[CH:6][CH:5]=[CH:4][N:3]=3)=[CH:9][CH:10]=2)[O:18]1

Participants

7

Reactant 4

HCID 962WaterHCID 62657Potassium Phosphate, TribasicHCID 783452-BromopyrimidineHCID 105924952,2'-(1,4-Phenylene)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane)

Product 1

HCID 583826142-(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyrimidineYield 28%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

A degassed solution of 2-bromopyrimidine (1.5 g, 9.4 mmol), 2,2′-(1,4-phenylene)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) (5.1 g, 16.0 mmol), 1.0 M aq K3PO4 (28.3 mL, 28.3 mmol), and Pd(PPh3)4 (330 mg, 0.31 mmol) in DMF (140 mL) was heated to 80° C. and stirred at this temperature for 16 h. Water (100 mL) was added to the reaction mixture and was extracted with EtOAc (3×200 mL). The combined organic phases were dried (Na2SO4), filtered, and concentrated under reduced pressure. The crude material was purified via flash chromatography using an eluent of 17% EtOAc in n-heptane to afford the title compound as a white solid (0.7 g, 28%). MS (LCMS) m/z 283.1 (M+1). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.36 (s, 12H) 7.19 (t, J=4.68 Hz, 1H) 7.93 (d, J=8.00 Hz, 2H) 8.43 (d, J=7.81 Hz, 2H) 8.81 (d, J=4.68 Hz, 2H).

Workup

  1. extractionwas extracted with EtOAc (3×200 mL)
  2. dry with materialThe combined organic phases were dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe crude material was purified via flash chromatography

Sources & evidence

ORD record
ord-6e12f8c9b9b34c15b1d783c183eae649
Source dataset
uspto-grants-2014_01
Patent number
US08624034B2

Reaction notes

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