Potassium Carbonate → HCID 89816095, compound

HRID 717568Notes

Reaction equation

HRID 717568 reaction equation
Cl[C:2]1[N:7]=[CH:6][N:5]=[C:4]2[N:8]([CH3:12])[N:9]=[CH:10][CH2:11][C:3]=12.[C:13]1(B(O)O)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1.O>[CH3:12][N:8]1[C:4]2[N:5]=[CH:6][N:7]=[C:2]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:3]=2[CH2:11][CH:10]=[N:9]1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 66827Phenylboronic AcidHCID 898160331456534-36-3

Product 1

HCID 89816095HCID 89816095, compoundYield 91.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

The 5-chloro-1-methyl-1,4-dihydropyridazino[3,4-d]pyrimidine (310 mg), phenyl boronic acid (208 mg) and potassium carbonate (235 mg) were dissolved in toluene (10 mL) and water (1.0 mL). The reaction mixture was degassed with nitrogen for 30 minutes and Pd(PPh3)4 (98 mg) was added. The reaction mixture was again degassed with nitrogen for 20 minutes and then heated to 100° C. for 1 hour 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 resulting crude product was purified by column chromatography using MeOH/CHCl3 (1.0:9.0) as eluent to afford 1-methyl-5-phenyl-1,4-dihydropyrimido[4,5-c]pyridazine (350 mg) as off white solid. 1H NMR (DMSO-d6): δ 3.41 (s, 3H), 3.52-3.53 (d, 2H), 6.86 (t, 1H), 7.47-7.49 (m, 3H), 7.56-7.60 (m, 2H), 8.66 (s, 1H).

Workup

  1. customThe reaction mixture was degassed with nitrogen for 30 minutes
  2. additionPd(PPh3)4 (98 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 resulting crude product was purified by column chromatography

Sources & evidence

ORD record
ord-373b0052f8b0428ca7172c17ec0a9e4d
Source dataset
uspto-grants-2015_11
Patent number
US09193725B2

Reaction notes

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