Potassium Carbonate → HCID 89815877, compound

HRID 717576Notes

Reaction equation

HRID 717576 reaction equation
Cl[C:2]1[N:7]=[CH:6][N:5]=[C:4]2[N:8]([CH3:13])[N:9]=[C:10]([CH3:12])[CH2:11][C:3]=12.[C:14]1(B(O)O)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1.O>[CH3:13][N:8]1[C:4]2=[N:5][CH:6]=[N:7][C:2]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[C:3]2[CH2:11][C:10]([CH3:12])=[N:9]1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 66827Phenylboronic AcidHCID 89816078HCID 89816078, compound

Product 1

HCID 89815877HCID 89815877, compoundYield 37.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

The 5-chloro-1,3-dimethyl-1,4-dihydropyridazino[3,4-d]pyrimidine (1.1 g), phenyl boronic acid (682 mg) and potassium carbonate (771 mg) were dissolved in toluene (15 mL) and water (1.5 mL). After the reaction mixture was degassed with nitrogen for 30 minute, Pd(PPh3)4 (323 mg) was added. The reaction mixture was again degassed with nitrogen for 20 minutes and then heated to 100° C. for 3 hours in a sealed tube. The reaction mixture was filtered through a celite pad and washed with ethyl acetate (2×20 mL). The combined filtrate was washed with water (10 mL) and brine (10 mL). The organic layer was dried over anhydrous Na2SO4 and concentrated. The residue was purified by column chromatography using MeOH/CHCl3 (0.8:9.2) as eluent to afford 1,3-dimethyl-5-phenyl-1,4-dihydropyridazino[3,4-d]pyrimidine (500 mg) as colorless viscous liquid. 1H NMR (DMSO-d6): δ 1.89 (s, 3H), 3.37 (s, 3H), 3.52 (s, 2H), 7.47-7.57 (m, 5H), 8.60 (s, 1H).

Workup

  1. customAfter the reaction mixture was degassed with nitrogen for 30 minute
  2. additionPd(PPh3)4 (323 mg) was added
  3. customThe reaction mixture was again degassed with nitrogen for 20 minutes
  4. filtrationThe reaction mixture was filtered through a celite pad
  5. washwashed with ethyl acetate (2×20 mL)
  6. washThe combined filtrate was washed with water (10 mL) and brine (10 mL)
  7. dry with materialThe organic layer was dried over anhydrous Na2SO4
  8. concentrationconcentrated
  9. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-cdec75f9bc5c44de9b54ff331838fa06
Source dataset
uspto-grants-2015_11
Patent number
US09193725B2

Reaction notes

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