Potassium Phosphate, Tribasic → 7-Methyl-3-[3'-(5-methyl-[1,2,4]oxadiazol-3-yl)biphenyl-3-yl]imidazo[1,2-a]pyrimidine

HRID 478239Notes

Reaction equation

HRID 478239 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][N:5]2[C:8]([C:11]3[CH:16]=[CH:15][CH:14]=[C:13](B4OC(C)(C)C(C)(C)O4)[CH:12]=3)=[CH:9][N:10]=[C:4]2[N:3]=1.Br[C:27]1[CH:28]=[C:29]([C:33]2[N:37]=[C:36]([CH3:38])[O:35][N:34]=2)[CH:30]=[CH:31][CH:32]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.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>[CH3:1][C:2]1[CH:7]=[CH:6][N:5]2[C:8]([C:11]3[CH:12]=[C:13]([C:31]4[CH:32]=[CH:27][CH:28]=[C:29]([C:33]5[N:37]=[C:36]([CH3:38])[O:35][N:34]=5)[CH:30]=4)[CH:14]=[CH:15][CH:16]=3)=[CH:9][N:10]=[C:4]2[N:3]=1

Participants

6

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 88951393-(3-Bromophenyl)-5-methyl-1,2,4-oxadiazoleHCID 180012787-Methyl-3-[3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)phenyl]imidazo[1,2-a]pyrimidine

Product 1

HCID 99692117-Methyl-3-[3'-(5-methyl-[1,2,4]oxadiazol-3-yl)biphenyl-3-yl]imidazo[1,2-a]pyrimidine

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

To a degassed solution of 7-methyl-3-[3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)phenyl]imidazo[1,2-a]pyrimidine (0.1 g, 0.29 mmol) in 1,4-dioxane (3 ml) was added 3-(3-bromophenyl)-5-methyl-[1,2,4]oxadiazole (0.142 g, 0.59 mmol) (prepared as described in WO 95/27692), potassium phosphate (189 mg, 0.89 mmol) and tetrakis(triphenylphosphine)palladium(0) (17 mg, 15 μmol) and the mixture heated at 90° C. for 18 h. After cooling to ambient temperature the solvent was evaporated in vacuo and the residue stirred with 10% methanol in dichloromethane. The solid material was removed by filtration and the filtrate applied to two preparative TLC plates (silica gel) and eluted with 5% methanol in dichloromethane. The appropriate band was collected and processed, affording a solid which was recrystallised from dichloromethane/ethyl acetate/isohexane to give 7-methyl-3-[3′-(5-methyl-[1,2,4]oxadiazol-3-yl)biphenyl-3-yl]imidazo[1,2-a]pyrimidine as a cream coloured solid (32 mg): δH (400 MHz, CDCl3) 2.67 (3H, s), 2.68 (3H, s), 6.79 (1H, d, J 7), 7.60-7.80 (5H, m), 7.87 (1H, s), 7.92 (1H, m), 8.10 (1H, dd, J 7 and 1), 8.32 (1H, s), 8.52 (1H, d, J 7); m/z (ES+) 368 (M++H).

Workup

  1. temperatureAfter cooling to ambient temperature the solvent
  2. customwas evaporated in vacuo
  3. customThe solid material was removed by filtration
  4. washeluted with 5% methanol in dichloromethane
  5. customThe appropriate band was collected
  6. customaffording a solid which
  7. customwas recrystallised from dichloromethane/ethyl acetate/isohexane

Sources & evidence

ORD record
ord-21984d210b9e4d95a89c5a602e1e2a42
Source dataset
uspto-grants-2003_11
Patent number
US06642229B2

Reaction notes

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