Potassium Carbonate → HCID 69079170, compound

HRID 1517435Notes

Reaction equation

HRID 1517435 reaction equation
[NH2:1][C:2]1[N:3]=[C:4]([O:13][CH2:14][C:15]([F:18])([F:17])[F:16])[C:5]2[N:11]=[C:10](Cl)[CH:9]=[CH:8][C:6]=2[N:7]=1.[F:19][C:20]1[CH:25]=[CH:24][C:23](B(O)O)=[CH:22][CH:21]=1.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.O.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>[NH2:1][C:2]1[N:3]=[C:4]([O:13][CH2:14][C:15]([F:18])([F:17])[F:16])[C:5]2[N:11]=[C:10]([C:23]3[CH:24]=[CH:25][C:20]([F:19])=[CH:21][CH:22]=3)[CH:9]=[CH:8][C:6]=2[N:7]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 2856454-Fluorophenylboronic acidHCID 86630380HCID 86630380, compound

Product 1

HCID 69079170HCID 69079170, compound

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a degassed suspension of 2-amino-4-(trifluoroethoxy)-6-chloro-pyrido[3,2-d]pyrimidine (24 mg, 0.1 mmol), 4-fluorophenyl boronic acid (21 mg, 0.15 mmol), and potassium carbonate (280 mg, 2.03 mmol) in a mixture of dioxane (15 ml) and water (5 ml) was added a catalytic amount of tetrakis(triphenylphosphine)palladium(0) (20 mg, 0.017 mmol). The mixture was refluxed for 45 minutes. The solvents were evaporated in vacuo, and the crude residue was purified by preparative TLC, using a mixture of methanol and dichloromethane (in a ratio of 10:90) as mobile phase, yielding the pure title compound, which was characterised by its mass spectrum as follows: MS (m/z): 339 ([M+H]+, 100).

Workup

  1. temperatureThe mixture was refluxed for 45 minutes
  2. customThe solvents were evaporated in vacuo
  3. customthe crude residue was purified by preparative TLC
  4. additiona mixture of methanol and dichloromethane (in a ratio of 10:90) as mobile phase

Sources & evidence

ORD record
ord-3f04bdb836b84e879fcb5786921fdcbf
Source dataset
uspto-grants-2012_07
Patent number
US08232278B2

Reaction notes

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