Sodium Hydroxide → HCID 18001299, compound

HRID 478234Notes

Reaction equation

HRID 478234 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]([C:9]2[N:13]3[CH:14]=[CH:15][C:16]([CH3:18])=[N:17][C:12]3=[N:11][CH:10]=2)[CH:6]=[CH:7][CH:8]=1.[OH-].[Na+]>Br.C(O)(=O)C>[CH3:18][C:16]1[CH:15]=[CH:14][N:13]2[C:9]([C:5]3[CH:4]=[C:3]([OH:2])[CH:8]=[CH:7][CH:6]=3)=[CH:10][N:11]=[C:12]2[N:17]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 18001308HCID 18001308, compound

Product 1

HCID 18001299HCID 18001299, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 260Hydrogen BromideSolvent2×

Conditions

Temperature
130 °C

Procedure

A mixture of 3-(3-methoxyphenyl)-7-methylimidazo[1,2-a]pyrimidine (5.02 g, 21 mmol) in hydrogen bromide (25 ml of a 30 wt. % solution in acetic acid) was heated at 130° C. for 8 h. A further portion of hydrogen bromide solution was added (25 ml) and heating continued for 16 h. The reaction was cooled to ambient temperature and diluted with ice-cold water (200 ml). The aqueous phase was made neutral with 4N sodium hydroxide then extracted with dichloromethane (2×250 ml). The organics were combined, washed with brine, dried over anhydrous magnesium sulfate, filtered and evaporated to dryness. The residue was triturated with ether to afford 3-(7-methylimidazo[1,2-a]pyrimidin-3-yl)-phenol as a light-grey solid (4.4 g, 93%): m/z (ES+) 226 (M++H).

Workup

  1. temperatureheating
  2. temperatureThe reaction was cooled to ambient temperature
  3. extractionthen extracted with dichloromethane (2×250 ml)
  4. washwashed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customevaporated to dryness
  8. customThe residue was triturated with ether

Sources & evidence

ORD record
ord-bb595a5d57c346cdad94f90755d65e97
Source dataset
uspto-grants-2003_11
Patent number
US06642229B2

Reaction notes

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