Sodium Carbonate → HCID 18507310, compound

HRID 1355687Notes

Reaction equation

HRID 1355687 reaction equation
I[C:2]1[C:3]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[N:4][C:5]([NH2:8])=[N:6][CH:7]=1.[C:15]1(B(O)O)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Pd]>[NH2:8][C:5]1[N:4]=[C:3]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:2]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:7][N:6]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 185076485-Iodo-4-phenyl-pyrimidin-2-ylamine

Product 1

HCID 18507310HCID 18507310, compoundYield 51%

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

To a stirred solution of 260 mg (0.88 mmol) 5-iodo-4-phenyl-pyrimidin-2-ylamine in 10 ml dioxane under argon at room temperature were added 112 mg (0.92 mmol) phenylboronic acid, 101 mg (0.09 mmol) tetrakis(triphenylphosphine)palladium(O) and 2.0 ml (4.0 mmol) 2M aqueous sodium carbonate solution. The reaction mixture was heated at reflux for 16 h, then cooled to room temperature, 1 g of kieselgel added, and the mixture concentrated in vacuo. Flash chromatography (1/1 ethyl acetate/hexane) followed by recrystallisation from ethyl acetate/pentane afforded 110 mg (51%) 2-amino-4,5-diphenylpyrimidine as a white crystalline solid. EI-MS m/e (%): 247 (M+, 90), 246 ([M—H]+, 100).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 16 h
  3. addition1 g of kieselgel added
  4. concentrationthe mixture concentrated in vacuo
  5. customFlash chromatography (1/1 ethyl acetate/hexane) followed by recrystallisation from ethyl acetate/pentane

Sources & evidence

ORD record
ord-194b04ae05f8445391a462c7747fa947
Source dataset
uspto-grants-2003_07
Patent number
US06586441B2

Reaction notes

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