Potassium Phosphate, Tribasic → HCID 10291463, compound

HRID 2184014Notes

Reaction equation

HRID 2184014 reaction equation
CC1(C)COB([C:8]2[CH:9]=[CH:10][C:11]([F:20])=[C:12]([C:14]3[CH:19]=[N:18][CH:17]=[CH:16][N:15]=3)[CH:13]=2)OC1.Br[C:23]1[N:27]2[CH:28]=[CH:29][C:30]([C:32]([OH:35])([CH3:34])[CH3:33])=[N:31][C:26]2=[N:25][CH:24]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>C1C=CC([PH+]([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.C1C=CC([PH+]([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.C(Cl)Cl.Cl[Pd]Cl.[Fe].CN(C)C=O>[F:20][C:11]1[CH:10]=[CH:9][C:8]([C:23]2[N:27]3[CH:28]=[CH:29][C:30]([C:32]([OH:35])([CH3:33])[CH3:34])=[N:31][C:26]3=[N:25][CH:24]=2)=[CH:13][C:12]=1[C:14]1[CH:19]=[N:18][CH:17]=[CH:16][N:15]=1

Participants

6

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 112422822-(3-Bromoimidazo[1,2-a]pyrimidin-7-yl)propan-2-olHCID 22473577HCID 22473577, compound

Product 1

HCID 10291463HCID 10291463, compound

Reagents, catalysts & solvents 2

HCID 53485975CID 53485975CatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
65 °C

Procedure

To 2-[5-(5,5-dimethyl-[1,3,2]dioxaborinan-2-yl)-2-fluorophenyl]pyrazine prepared above was added 2-(3-bromoimidazo[1,2-α]pyrimidin-7-yl)propan-2-ol (0.266 g, 1.04 mmol) followed by dry potassium phosphate (0.065 g), dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium(II) dichloromethane adduct (0.06 g) and dry N,N-dimethylformamide (5 ml). The mixture was degassed with nitrogen then stirred for 16 h at 65° C. under an atmosphere of dry nitrogen. The reaction was cooled to ambient temperature, silica gel added, and the solvent stripped at reduced pressure. The residue was subjected to chromatography on silica gel eluting with dichloromethane on a gradient of methanol (3.5-5%). The appropriate fractions were combined, concentrated in vacuo and the residue crystallised from toluene to afford 2-[3-(4-fluoro-3-(pyrazin-2-yl)phenyl)imidazo[1,2-α]pyrimidin-7-yl]propan-2-ol: δH (400 MHz, DMSO) 1.51 (6H, s), 5.51 (1H, s), 7.41 (1H, d, J 7), 7.62 (1H, dd, J 11 and 9), 7.88 (1H, m), 7.95 (1H, s), 8.18 (1H, dd, J 7 and 2), 8.72 (1H, d, J 2), 8.84 (1H, dd, J 1 and 2), 8.99 (1H, d, J 7), 9.14 (1H, dd, J 2 and 2); m/z (ES+) 350 (MH+).

Workup

  1. customThe mixture was degassed with nitrogen
  2. temperatureThe reaction was cooled to ambient temperature
  3. additionsilica gel added
  4. concentrationconcentrated in vacuo
  5. customthe residue crystallised from toluene

Sources & evidence

ORD record
ord-c0ce67f1777449c1b3c2fa39fe61ab44
Source dataset
uspto-grants-2005_05
Patent number
US06900215B2

Reaction notes

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