2-Amino-5-bromopyrimidine → 6-((6-Bromoimidazo[1,2-a]pyrimidin-3-yl)methyl)quinoline

HRID 456118Notes

Reaction equation

HRID 456118 reaction equation
ClC(CC1C=C2C(=CC=1)N=CC=C2)C=O.BrC1C=NC(N)=NC=1.[Br:24][C:25]1[CH:26]=[N:27][C:28]2[N:29]([CH:31]=[C:32]([CH2:34][C:35]3[CH:36]=[C:37]4[C:42](=[CH:43][CH:44]=3)[N:41]=[CH:40][CH:39]=[CH:38]4)[N:33]=2)[CH:30]=1>CC(O)(CC)C>[Br:24][C:25]1[CH:26]=[N:27][C:28]2[N:33]([C:32]([CH2:34][C:35]3[CH:36]=[C:37]4[C:42](=[CH:43][CH:44]=3)[N:41]=[CH:40][CH:39]=[CH:38]4)=[CH:31][N:29]=2)[CH:30]=1

Participants

5

Reactant 3

HCID 2313102-Amino-5-bromopyrimidineHCID 575165372-Chloro-3-(quinolin-6-yl)propanalHCID 669271896-(6-Bromo-imidazo[1,2-a]pyrimidin-2-ylmethyl)quinoline

Product 1

HCID 581904746-((6-Bromoimidazo[1,2-a]pyrimidin-3-yl)methyl)quinoline

Reagents, catalysts & solvents 1

HCID 64052-Methyl-2-butanolSolvent

Procedure

A solution of 2-chloro-3-(quinolin-6-yl)propanal (1.0 g, 2.54 mmol) and 5-bromopyrimidin-2-amine (0.53 g, 3.05 mmol) in 2-methyl-butan-2-ol (10 mL) was stirred at 135° C. for 12 h. After cooling, the solvent was removed in vacuo and the residue was purified by flash chromatography in silica gel eluting with a CH2Cl2/MeOH gradient to afford a mixture of the title compound and 6-(6-bromo-imidazo[1,2-a]pyrimidin-2-ylmethyl)quinoline (250 mg, 29%) as brown solid. LCMS (method E): [MH]+=339/341, tR=3.51 min.

Workup

  1. temperatureAfter cooling
  2. customthe solvent was removed in vacuo
  3. customthe residue was purified by flash chromatography in silica gel eluting with a CH2Cl2/MeOH gradient
  4. customto afford

Sources & evidence

ORD record
ord-ddc2399e211942689e584b2b87243f0c
Source dataset
uspto-grants-2013_07
Patent number
US08497368B2

Reaction notes

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