Isopropanol → HCID 86621435, compound

HRID 878447Notes

Reaction equation

HRID 878447 reaction equation
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[CH:4][N:3]=1.CC1(C)C(C)(C)OB([C:17]2[CH:18]=[N:19][N:20]([C:22]([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH:21]=2)O1.C(=O)([O-])[O-].[Na+].[Na+].CC(O)C>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O>[Cl:8][C:6]1[CH:7]=[C:2]([C:17]2[CH:18]=[N:19][N:20]([C:22]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)([C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)[C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[CH:21]=2)[N:3]=[CH:4][N:5]=1

Participants

7

Reactant 4

HCID 3776IsopropanolHCID 10340Sodium CarbonateHCID 709434,6-DichloropyrimidineHCID 457896834-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-1-trityl-1H-pyrazole

Product 1

HCID 86621435HCID 86621435, compound

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolvent

Conditions

Temperature
108 °C

Procedure

In a microwave reaction tube were combined 4,6-dichloropyrimidine (480 mg, 3.22 mmol), 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-trityl-1H-pyrazole (1.28 g, 2.93 mmol; JP 2005232071), bis(triphenylphosphine)-palladium(II) chloride (82 mg, 0.117 mmol), sodium carbonate (776 mg, 7.32 mmol), followed by the solvents 2-propanol (9.0 mL) and water (3.0 mL). The tube was sealed, and the reaction was heated to 108° C. for 30 minutes in the microwave reactor. After cooling to room temperature, the mixture was partitioned between ethyl acetate (2×100 mL) and water (200 mL). The combined organic extracts were washed with brine, dried (sodium sulfate) and concentrated under reduced pressure, and the resulting material was purified by silica gel flash column chromatography to afford the titled compound: 1H NMR (300 MHz, methanol-D4) δ ppm 7.11-7.22 (m, 6H), 7.28-7.41 (m, 9H), 7.81-7.83 (m, 1H), 8.23-8.26 (m, 1H), 8.30 (s, 1H), 8.75-8.78 (m, 1H). MS (DCI/NH3) m/z=423 (M+H)+.

Workup

  1. customIn a microwave reaction tube
  2. customThe tube was sealed
  3. temperatureAfter cooling to room temperature
  4. customthe mixture was partitioned between ethyl acetate (2×100 mL) and water (200 mL)
  5. washThe combined organic extracts were washed with brine
  6. dry with materialdried (sodium sulfate)
  7. concentrationconcentrated under reduced pressure
  8. customthe resulting material was purified by silica gel flash column chromatography

Sources & evidence

ORD record
ord-9aff0f53eb1d4e8f8243cb455053e2a2
Source dataset
uspto-grants-2015_03
Patent number
US08987453B2

Reaction notes

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