Sodium Carbonate → HCID 18001308, compound

HRID 478233Notes

Reaction equation

HRID 478233 reaction equation
Br[C:2]1[N:6]2[CH:7]=[CH:8][C:9]([CH3:11])=[N:10][C:5]2=[N:4][CH:3]=1.[CH3:12][O:13][C:14]1[CH:15]=[C:16](B(O)O)[CH:17]=[CH:18][CH:19]=1.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.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>[NH3:4].[CH3:12][O:13][C:14]1[CH:19]=[C:18]([C:2]2[N:6]3[CH:7]=[CH:8][C:9]([CH3:11])=[N:10][C:5]3=[N:4][CH:3]=2)[CH:17]=[CH:16][CH:15]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 2734370(3-Methoxyphenyl)boronic acidHCID 114015833-Bromo-7-methylimidazo[1,2-a]pyrimidine

Product 2

HCID 222AmmoniaHCID 18001308HCID 18001308, compoundYield 177.2%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of 3-bromo-7-methylimidazo[1,2-a]pyrimidine (5.3 g, 25 mmol), 3-methoxyphenylboronic acid (4.94 g, 32.5 mmol) and tetrakis(triphenylphosphine)palladium(0) (870 mg, 0.8 mmol) in 1,2-dimethoxyethane (40 ml) was treated with sodium carbonate (18.8 ml of a 2M aqueous solution) then heated at 85° C. for 16 h. The reaction mixture was allowed to cool to ambient temperature then partitioned between ethyl acetate and water. The organics were washed with 10% sodium carbonate solution, water, brine, dried over anhydrous magnesium sulfate, filtered then pre-adsorbed onto silica. Purification by chromatography on silica gel eluting with dichloromethane:conc. ammonia (99.5:0.5) on a gradient of methanol (1-3%) afforded 3-(3-methoxyphenyl)-7-methylimidazo[1,2-a]pyrimidine as a cream-coloured solid (5.3 g, 89%): δH (400 MHz, CDCl3) 2.66 (3H, s), 3.87 (3H, s), 6.76 (1H, d, J 7), 6.95-6.98 (1H, m), 7.03-7.05 (1H, m), 7.09-7.11 (1H, m), 7.44 (1H, t, J 8), 7.80 (1H, s), 8.52 (1H, d, J 7); m/z (ES+) 240 (M++H).

Workup

  1. temperatureto cool to ambient temperature
  2. customthen partitioned between ethyl acetate and water
  3. washThe organics were washed with 10% sodium carbonate solution, water, brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customPurification by chromatography on silica gel eluting with dichloromethane

Sources & evidence

ORD record
ord-930ee501f76f4b129446cfa4f8af4c65
Source dataset
uspto-grants-2003_11
Patent number
US06642229B2

Reaction notes

Loading…