Sodium Carbonate → HCID 59585163, compound

HRID 220066Notes

Reaction equation

HRID 220066 reaction equation
O1CCOCC1.Cl[C:8]1[N:13]=[CH:12][N:11]=[C:10]([NH:14][CH:15]2[CH2:17][CH2:16]2)[C:9]=1[NH2:18].C(=O)([O-])[O-].[Na+].[Na+].[Cl:25][C:26]1[CH:31]=[CH:30][C:29](B(O)O)=[CH:28][CH:27]=1>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.O>[Cl:25][C:26]1[CH:31]=[CH:30][C:29]([C:8]2[N:13]=[CH:12][N:11]=[C:10]([NH:14][CH:15]3[CH2:17][CH2:16]3)[C:9]=2[NH2:18])=[CH:28][CH:27]=1

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 312751,4-DioxaneHCID 742994-Chlorophenylboronic acidHCID 105117206-chloro-N4-cyclopropylpyrimidine-4,5-diamine

Product 1

HCID 59585163HCID 59585163, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

In a reactor carousel test tube which had been dried by heating and preheated to 100° C., the degassed diluent mixture dioxane (20 ml)/water (7 ml) was added to 6-chloro-N-cyclopropylpyrimidine-4,5-diamine (10 g, 54.1 mmol) and sodium carbonate (17.22 g, 162 mmol). 5 mol % of tetrakis(triphenylphosphine)palladium(0) and 4-chlorophenylboronic acid (108.2 mmol) were added, and the reaction mixture was stirred at 90° C. overnight. The solution was cooled, filtered and concentrated and the residue was recrystallised from acetonitrile.

Workup

  1. customIn a reactor carousel test tube which had been dried
  2. temperatureby heating
  3. custompreheated to 100° C.
  4. temperatureThe solution was cooled
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customthe residue was recrystallised from acetonitrile

Sources & evidence

ORD record
ord-8059151c01d1486fbd9aadcf0d65f924
Source dataset
uspto-grants-2012_06
Patent number
US08202877B2

Reaction notes

Loading…