Potassium Carbonate → 6-(2-Bromophenyl)-4-(morpholin-4-yl)pyrido[3,2-d]pyrimidin-2-amine

HRID 1517424Notes

Reaction equation

HRID 1517424 reaction equation
[NH2:1][C:2]1[N:3]=[C:4]([N:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)[C:5]2[N:11]=[C:10](Cl)[CH:9]=[CH:8][C:6]=2[N:7]=1.C(=O)([O-])[O-].[K+].[K+].[Br:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1B(O)O>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]([N:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)[C:5]2[N:11]=[C:10]([C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=3[Br:25])[CH:9]=[CH:8][C:6]=2[N:7]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 2773294(2-Bromophenyl)boronic acidHCID 576983306-Chloro-4-(morpholin-4-yl)pyrido[3,2-d]pyrimidin-2-amine

Product 1

HCID 689184916-(2-Bromophenyl)-4-(morpholin-4-yl)pyrido[3,2-d]pyrimidin-2-amineYield 30%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent2×

Procedure

A solution of 2-amino-4-morpholino-6-chloro-pyrido[3,2-d]pyrimidine (265 mg, 1 mmol), potassium carbonate (690 mg, 5 mmol), tetrakis(triphenylphosphine)palladium(0) (100 mg) in dioxane (10 ml) and water (3 ml) was refluxed. To this refluxing solution was added dropwise (with a speed of 0.25 ml/min) a solution of 2-bromo-phenyl boronic acid (220 mg, 1.1 mmol) in dioxane (2 ml). Once the addition was complete, the reaction mixture was refluxed for another 2 hours. The reaction mixture was cooled down and the solvents were evaporated in vacuo. The residue was redissolved in dichloromethane and extracted with water. The combined organic layers were dried over Na2SO4 and the crude residue was purified by preparative TLC on silica, using a methanol/dichloromethane mixture in a ratio of 10:90 as mobile phase, yielding the pure title compound (100 mg, yield: 30%) which was characterised as follows: MS (m/z): 386, 388 ([M+H]+, 100).

Workup

  1. additionOnce the addition
  2. temperaturethe reaction mixture was refluxed for another 2 hours
  3. temperatureThe reaction mixture was cooled down
  4. customthe solvents were evaporated in vacuo
  5. dissolutionThe residue was redissolved in dichloromethane
  6. extractionextracted with water
  7. dry with materialThe combined organic layers were dried over Na2SO4
  8. customthe crude residue was purified by preparative TLC on silica

Sources & evidence

ORD record
ord-425f58052fb54461be305b0ac3bb986a
Source dataset
uspto-grants-2012_07
Patent number
US08232278B2

Reaction notes

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