Hydrochloric Acid → 4-(3-bromophenyl)pyrimidin-2-amine

HRID 1818531Notes

Reaction equation

HRID 1818531 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9](=O)[CH2:10]N(C)C)[CH:5]=[CH:6][CH:7]=1.[Cl-].[NH2:16][C:17]([NH2:19])=[NH2+:18].[O-]CC.[Na+].Cl>CCO>[Br:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:9]=[CH:10][N:16]=[C:17]([NH2:19])[N:18]=2)[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 2723922Sodium ethoxideHCID 5460839Carbamimidoylazanium ChlorideHCID 68821237HCID 68821237, compound

Product 1

HCID 46097874-(3-bromophenyl)pyrimidin-2-amineYield 31.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Combine 1-(3-bromo-phenyl)-3-dimethylamino-propanone (3.00 g, 11.8 mmol) and guanidinium chloride (1.12 g, 11.8 mmol), sodium ethoxide (5 mL, 21% wt solution in ethanol), absolute EtOH (24 mL) and heat to reflux overnight. Cool to room temperature and pour into 1% hydrochloric acid (200 mL). Extract with ethyl acetate, dry over sodium sulfate and condense to afford 4-(3-bromo-phenyl)-pyrimidin-2-ylamine (930 mg, 3.72 mmol) as a white solid. MS (m/z): 250.2 (M).

Workup

  1. temperatureto reflux overnight
  2. extractionExtract with ethyl acetate
  3. dry with materialdry over sodium sulfate and condense

Sources & evidence

ORD record
ord-9425a6df6b894ce2862544b50d691171
Source dataset
uspto-grants-2009_10
Patent number
US07598423B2

Reaction notes

Loading…